Compound having naphthobenzofuranyl structure, material for organic electroluminescence device, organic electroluminescence device, and electronic instrument

ABSTRACT

A compound represented by the following formula (1): 
                         
The R 1  to R 9 , L 1  to L 3 , and Ar 1  to Ar 2  in the formula (1) are as defined in the description. An organic electroluminescence device contains the compound, and an electronic instrument includes the organic electroluminescence device.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation of International Application No.PCT/JP2021/040498 filed on Nov. 4, 2021 and claims priority to Japaneseapplication No. 2020-185314 filed on Nov. 5, 2020, the disclosures ofall of which are incorporated herein by reference in their entireties.

TECHNICAL FIELD

The present invention relates to a compound, a material for organicelectroluminescence devices, an organic electroluminescence device, andan electronic instrument including the organic electroluminescencedevice.

BACKGROUND ART

In general, an organic electroluminescence device (hereinafter sometimesreferred to as “organic EL device”) is composed of an anode, a cathode,and an organic layer interposed between the anode and the cathode. Inapplication of a voltage between the two electrodes, electrons from thecathode side and holes from the anode side are injected into a lightemitting region, and the injected electrons and holes are recombined inthe light emitting region to generate an excited state, which thenreturns to the ground state to emit light. Accordingly, it is important,for providing a high-performance organic EL device, to develop amaterial that efficiently transports electrons or holes into a lightemitting region to promote recombination of the electrons and holes.

PTLs 1 to 8 disclose compounds for use as a material for organicelectroluminescence devices.

CITATION LIST Patent Literature

-   PTL 1: KR 2076958 B1-   PTL 2: KR 2019-0007789 A-   PTL 3: CN 108689972 A-   PTL 4: CN 108658932 A-   PTL 5: CN 108947902 A-   PTL 6: KR 2020-0056059 A-   PTL 7: KR 2020-0053284 A-   PTL 8: US 2018/0083197 A1

SUMMARY OF INVENTION Technical Problem

Although many compounds for organic EL devices have conventionally beenreported, a compound that further enhances performance of an organic ELdevice is still desired.

The present invention has been made for solving the above problem, andhas an object to provide a compound that further improves performance ofan organic EL device, an organic EL device having further improveddevice performance, and an electronic instrument including such anorganic EL device.

Solution to Problem

As a result of intensive and extensive studies about the compoundsdisclosed in the above patent literatures and the performance of organicEL devices including the compounds, the present inventors have foundthat a monoamine represented by the following formula (1) provides anorganic EL device having further improved device performance.

In an aspect, the present invention provides a compound represented bythe following formula (1):

wherein

R¹ to R⁹ are each independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, ahalogen atom, a cyano group, a nitro group, or a substituted orunsubstituted heterocyclic group having 5 to 50 ring atoms,

provided that

adjacent two selected from R¹ to R⁹ are not bonded to each other, thusforming no ring structure,

L¹ is a substituted or unsubstituted arylene group having 6 to 30 ringcarbon atoms or a substituted or unsubstituted divalent heterocyclicgroup having 5 to 30 ring atoms, and

L² and L³ are each independently a single bond, a substituted orunsubstituted divalent heterocyclic group having 5 to 30 ring atoms, ora group represented by any of the following formulae (i) to (iii):

wherein

-   -   *a is bonded to one selected from the carbon atoms *1 to *3,    -   *b is bonded to one selected from the carbon atoms *4 to *6,    -   *c is bonded to one selected from the carbon atoms *7 to *9,    -   *d is bonded to one selected from the carbon atoms *10 to *17,        *e is bonded to another one selected from the carbon atoms *10        to *17,    -   * represents a bonding site to the central nitrogen atom, and    -   ** represents a bonding site to Ar¹ or Ar²,

Ar¹ and Ar² are each independently a group represented by any of thefollowing formulae (a) to (e):

in the formula (a),

-   -   R¹⁰ to R²⁵ are each independently a hydrogen atom, a substituted        or unsubstituted alkyl group having 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group having 3 to 50        ring carbon atoms, a halogen atom, a cyano group, a nitro group,        a substituted or unsubstituted aryl group having 6 to 30 ring        carbon atoms constituted only of 6-membered rings, or a        substituted or unsubstituted heterocyclic group having 5 to 50        ring atoms.    -   provided that    -   one selected from R¹⁰ to R¹⁴ is a single bond bonded to *f,    -   one selected from R¹⁵ to R²⁰ is a single bond bonded to *g,        another one selected from R¹¹ to R²⁰ is a single bond bonded to        *h,    -   ** represents a bonding site to L² or L³,    -   m1 is 0 or 1, n1 is 0 or 1,    -   when m1 is 0 and n1 is 0, *h is bonded to L² or L³,    -   when m1 is 0 and n1 is 1, *f is bonded to L² or L³,    -   when m1 is 1 and n1 is 0, one selected from R¹⁰ to R¹⁴ is a        single bond bonded to *h,    -   k1 is 1 or 2, and    -   adjacent two selected from R¹⁰ to R¹⁴ that are not the single        bond are, and adjacent two selected from R¹⁵ to R²⁰ that are not        either of the single bonds are, not bonded to each other, thus        forming no ring structure;

in the formula (b),

-   -   R¹⁰ to R²⁰, *f, *g, *h, and *** are the same as described above,    -   R²⁶ to R³³ are each independently a hydrogen atom, a substituted        or unsubstituted alkyl group having 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group having 3 to 50        ring carbon atoms, a halogen atom, a cyano group, a nitro group,        a substituted or unsubstituted aryl group having 6 to 30 ring        carbon atoms constituted only of 6-membered rings, or a        substituted or unsubstituted heterocyclic group having 5 to 50        ring atoms,    -   provided that one selected from R²⁶ to R³³ is a single bond        bonded to *i,    -   m2 is 0 or 1, n2 is 0 or 1,    -   when m2 is 0 and n2 is 0, *h is bonded to L² or L³,    -   when m2 is 0 and n2 is 1, *f is bonded to L² or L³,    -   when m2 is 1 and n2 is 0, one selected from R¹⁰ to R¹⁴ is a        single bond bonded to *h, and    -   adjacent two selected from R¹⁰ to R¹⁴ that are not the single        bond are, and adjacent two selected from R¹⁵ to R²⁰ that are not        either of the single bonds are, not bonded to each other, thus        forming no ring structure;

in the formula (c),

-   -   R¹⁰ to R²⁰, *f, *g, *h, and *** are the same as described above,    -   R³⁴ to R⁴³ are each independently a hydrogen atom, a substituted        or unsubstituted alkyl group having 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group having 3 to 50        ring carbon atoms, a halogen atom, a cyano group, a nitro group,        a substituted or unsubstituted aryl group having 6 to 30 ring        carbon atoms constituted only of 6-membered rings, or a        substituted or unsubstituted heterocyclic group having 5 to 50        ring atoms,    -   provided that one selected from R³⁴ to R⁴³ is a single bond        bonded to *j,    -   m3 is 0 or 1, n3 is 0 or 1,    -   when m3 is 0 and n3 is 0, *h is bonded to L² or L³,    -   when m3 is 0 and n3 is 1, *f is bonded to L² or L,    -   when m3 is 1 and n2 is 0, one selected from R¹⁰ to R¹⁴ is a        single bond bonded to *h, and    -   adjacent two selected from R¹⁰ to R¹⁴ that are not the single        bond are, adjacent two selected from R¹⁵ to R²⁰ that are not        either of the single bonds are, and R³⁴ and R³⁵ are, not bonded        to each other, thus forming no ring structure;

in the formula (d),

-   -   R¹⁰ to R¹⁴, *f, and *** are the same as described above,    -   R⁴⁴ to R⁵¹ are each independently a hydrogen atom, a substituted        or unsubstituted alkyl group having 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group having 3 to 50        ring carbon atoms, a halogen atom, a cyano group, a nitro group,        a substituted or unsubstituted aryl group having 6 to 30 ring        carbon atoms constituted only of 6-membered rings, or a        substituted or unsubstituted heterocyclic group having 5 to 50        ring atoms,    -   X is an oxygen atom, a sulfur atom, CR^(a)R^(b), or NR^(C),    -   R^(a), R^(b), and R^(c) are each independently a hydrogen atom,        a substituted or unsubstituted alkyl group having 1 to 50 carbon        atoms, a substituted or unsubstituted aryl group having 6 to 50        ring carbon atoms, or a substituted or unsubstituted        heterocyclic group having 5 to 50 ring atoms,    -   provided that one selected from R⁴⁴ to R⁵¹ and R^(c) is a single        bond bonded to *k.    -   m4 is 0 or 1,    -   when m4 is 0. *f is bonded to L² or L³,    -   combinations of adjacent two selected from R⁴⁴ to R⁵¹ that are        not the single bond may each independently be bonded to each        other to form a substituted or unsubstituted ring structure, and    -   R^(a) and R^(b) are not crosslinked;

in the formula (e),

-   -   R¹⁰ to R¹⁴, *f, and *** are the same as described above,    -   R⁵² to R⁶⁶ are each independently a hydrogen atom, a substituted        or unsubstituted alkyl group having 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group having 3 to 50        ring carbon atoms, a halogen atom, a cyano group, a nitro group,        a substituted or unsubstituted aryl group having 6 to 30 ring        carbon atoms constituted only of 6-membered rings, or a        substituted or unsubstituted heterocyclic group having 5 to 50        ring atoms,    -   provided that    -   one selected from R⁵² to R⁵⁶ is a single bond bonded to *l,        another one selected from R⁵² to R⁵⁶ is a single bond bonded to        *m,    -   m5 is 0 or 1,    -   when m5 is 0, *f is bonded to L² or L³,    -   adjacent two selected from R¹⁰ to R¹⁴ that are not the single        bond are, adjacent two selected from R⁵² to R⁵⁶ that are not        either of the single bonds are, R⁵² and R⁶¹ are, and R⁵⁶ and R⁵⁷        are, not bonded to each other, thus forming no ring structure.

In another aspect, the present invention provides a material for organicEL devices, the material containing the compound represented by theformula (1).

In still another aspect, the present invention provides an organicelectroluminescence device including an anode, a cathode, and an organiclayer disposed between the anode and the cathode, the organic layerincluding a light emitting layer, at least one layer of the organiclayer containing the compound represented by the formula (1).

In still yet another aspect, the present invention provides anelectronic instrument including the organic electroluminescence device.

Advantageous Effects of Invention

The organic EL device containing the compound represented by the formula(1) shows an improved device performance.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 is a schematic diagram illustrating an example of the layerconfiguration of the organic EL device according to an aspect of thepresent invention.

FIG. 2 is a schematic diagram illustrating another example of the layerconfiguration of the organic EL device according to an aspect of thepresent invention.

DESCRIPTION OF EMBODIMENTS Definitions

In the description herein, the hydrogen atom encompasses isotopesthereof having different numbers of neutrons, i.e., a light hydrogenatom (protium), a heavy hydrogen atom (deuterium), and tritium.

In the description herein, the bonding site where the symbol, such as“R”, or “D” representing a deuterium atom is not shown is assumed tohave a hydrogen atom, i.e., a protium atom, a deuterium atom, or atritium atom, bonded thereto.

In the description herein, the number of ring carbon atoms shows thenumber of carbon atoms among the atoms constituting the ring itself of acompound having a structure including atoms bonded to form a ring (suchas a monocyclic compound, a condensed ring compound, a bridged compound,a carbocyclic compound, and a heterocyclic compound). In the case wherethe ring is substituted by a substituent, the carbon atom contained inthe substituent is not included in the number of ring carbon atoms. Thesame definition is applied to the “number of ring carbon atoms”described hereinafter unless otherwise indicated. For example, a benzenering has 6 ring carbon atoms, a naphthalene ring has 10 ring carbonatoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4ring carbon atoms. For example, 9,9-diphenylfluorenyl group has 13 ringcarbon atoms, and 9,9′-spirobifluorenyl group has 25 ring carbon atoms.

In the case where a benzene ring has, for example, an alkyl groupsubstituted thereon as a substituent, the number of carbon atoms of thealkyl group is not included in the number of ring carbon atoms of thebenzene ring. Accordingly, a benzene ring having an alkyl groupsubstituted thereon has 6 ring carbon atoms. In the case where anaphthalene ring has, for example, an alkyl group substituted thereon asa substituent, the number of carbon atoms of the alkyl group is notincluded in the number of ring carbon atoms of the naphthalene ring.Accordingly, a naphthalene ring having an alkyl group substitutedthereon has 10 ring carbon atoms.

In the description herein, the number of ring atoms shows the number ofatoms constituting the ring itself of a compound having a structureincluding atoms bonded to form a ring (such as a monocyclic ring, acondensed ring, and a set of rings) (such as a monocyclic compound, acondensed ring compound, a bridged compound, a carbocyclic compound, anda heterocyclic compound). The atom that does not constitute the ring(such as a hydrogen atom terminating the bond of the atom constitutingthe ring) and, in the case where the ring is substituted by asubstituent, the atom contained in the substituent are not included inthe number of ring atoms. The same definition is applied to the “numberof ring atoms” described hereinafter unless otherwise indicated. Forexample, a pyridine ring has 6 ring atoms, a quinazoline ring has 10ring atoms, and a furan ring has 5 ring atoms. For example, the numberof hydrogen atoms bonded to a pyridine ring or atoms constituting asubstituent is not included in the number of ring atoms of the pyridinering. Accordingly, a pyridine ring having a hydrogen atom or asubstituent bonded thereto has 6 ring atoms. For example, the number ofhydrogen atoms bonded to carbon atoms of a quinazoline ring or atomsconstituting a substituent is not included in the number of ring atomsof the quinazoline ring. Accordingly, a quinazoline ring having ahydrogen atom or a substituent bonded thereto has 10 ring atoms.

In the description herein, the expression “having XX to YY carbon atoms”in the expression “substituted or unsubstituted ZZ group having XX to YYcarbon atoms” means the number of carbon atoms of the unsubstituted ZZgroup, and, in the case where the ZZ group is substituted, the number ofcarbon atoms of the substituent is not included. Herein, “YY” is largerthan “XX”, “XX” represents an integer of 1 or more, and “YY” representsan integer of 2 or more.

In the description herein, the expression “having XX to YY atoms” in theexpression “substituted or unsubstituted ZZ group having XX to YY atoms”means the number of atoms of the unsubstituted ZZ group, and, in thecase where the ZZ group is substituted, the number of atoms of thesubstituent is not included. Herein, “YY” is larger than “XX”, “XX”represents an integer of 1 or more, and “YY” represents an integer of 2or more.

In the description herein, an unsubstituted ZZ group means the casewhere the “substituted or unsubstituted ZZ group” is an “unsubstitutedZZ group”, and a substituted ZZ group means the case where the“substituted or unsubstituted ZZ group” is a “substituted ZZ group”.

In the description herein, the expression “unsubstituted” in theexpression “substituted or unsubstituted ZZ group” means that hydrogenatoms in the ZZ group are not substituted by a substituent. The hydrogenatoms in the “unsubstituted ZZ group” each are a protium atom, adeuterium atom, or a tritium atom.

In the description herein, the expression “substituted” in theexpression “substituted or unsubstituted ZZ group” means that one ormore hydrogen atom in the ZZ group is substituted by a substituent. Theexpression “substituted” in the expression “BB group substituted by anAA group” similarly means that one or more hydrogen atom in the BB groupis substituted by the AA group.

Substituents in Description

The substituents described in the description herein will be explained.

In the description herein, the number of ring carbon atoms of the“unsubstituted aryl group” is 6 to 50, preferably 6 to 30, and morepreferably 6 to 18, unless otherwise indicated in the description.

In the description herein, the number of ring atoms of the“unsubstituted heterocyclic group” is 5 to 50, preferably 5 to 30, andmore preferably 5 to 18, unless otherwise indicated in the description.

In the description herein, the number of carbon atoms of the“unsubstituted alkyl group” is 1 to 50, preferably 1 to 20, and morepreferably 1 to 6, unless otherwise indicated in the description.

In the description herein, the number of carbon atoms of the“unsubstituted alkenyl group” is 2 to 50, preferably 2 to 20, and morepreferably 2 to 6, unless otherwise indicated in the description.

In the description herein, the number of carbon atoms of the“unsubstituted alkynyl group” is 2 to 50, preferably 2 to 20, and morepreferably 2 to 6, unless otherwise indicated in the description.

In the description herein, the number of ring carbon atoms of the“unsubstituted cycloalkyl group” is 3 to 50, preferably 3 to 20, andmore preferably 3 to 6, unless otherwise indicated in the description.

In the description herein, the number of ring carbon atoms of the“unsubstituted arylene group” is 6 to 50, preferably 6 to 30, and morepreferably 6 to 18, unless otherwise indicated in the description.

In the description herein, the number of ring atoms of the“unsubstituted divalent heterocyclic group” is 5 to 50, preferably 5 to30, and more preferably 5 to 18, unless otherwise indicated in thedescription.

In the description herein, the number of carbon atoms of the“unsubstituted alkylene group” is 1 to 50, preferably 1 to 20, and morepreferably 1 to 6, unless otherwise indicated in the description.

Substituted or Unsubstituted Aryl Group

In the description herein, specific examples (set of specific examplesG1) of the “substituted or unsubstituted aryl group” include theunsubstituted aryl groups (set of specific examples G1A) and thesubstituted aryl groups (set of specific examples G1B) shown below.(Herein, the unsubstituted aryl group means the case where the“substituted or unsubstituted aryl group” is an “unsubstituted arylgroup”, and the substituted aryl group means the case where the“substituted or unsubstituted aryl group” is a “substituted arylgroup”.) In the description herein, the simple expression “aryl group”encompasses both the “unsubstituted aryl group” and the “substitutedaryl group”.

The “substituted aryl group” means a group formed by substituting one ormore hydrogen atom of the “unsubstituted aryl group” by a substituent.Examples of the “substituted aryl group” include groups formed by one ormore hydrogen atom of each of the “unsubstituted aryl groups” in the setof specific examples G1A by a substituent, and the examples of thesubstituted aryl groups in the set of specific examples G1B. Theexamples of the “unsubstituted aryl group” and the examples of the“substituted aryl group” enumerated herein are mere examples, and the“substituted aryl group” in the description herein encompasses groupsformed by substituting a hydrogen atom bonded to the carbon atom of thearyl group itself of each of the “substituted aryl groups” in the set ofspecific examples G1B by a substituent, and groups formed bysubstituting a hydrogen atom of the substituent of each of the“substituted aryl groups” in the set of specific examples G1B by asubstituent.

Unsubstituted Aryl Group (Set of Specific Examples G1A):

a phenyl group,

a p-biphenyl group,

a m-biphenyl group,

an o-biphenyl group,

a p-terphenyl-4-yl group,

a p-terphenyl-3-yl group,

a p-terphenyl-2-yl group,

a m-terphenyl-4-yl group,

a m-terphenyl-3-yl group,

a m-terphenyl-2-yl group,

an o-terphenyl-4-yl group,

an o-terphenyl-3-yl group,

an o-terphenyl-2-yl group,

a 1-naphthyl group,

a 2-naphthyl group,

an anthryl group,

a benzanthryl group,

a phenanthryl group,

a benzophenanthryl group,

a phenarenyl group,

a pyrenyl group,

a chrysenyl group,

a benzochrysenyl group,

a triphenylenyl group,

a benzotriphenylenyl group,

a tetracenyl group,

a pentacenyl group,

a fluorenyl group,

a 9,9′-spirobifluorenyl group,

a benzofluorenyl group,

a dibenzofluorenyl group,

a fluoranthenyl group,

a benzofluoranthenyl group,

a perylenyl group, and

monovalent aryl groups derived by removing one hydrogen atom from eachof the ring structures represented by the following general formulae(TEMP-1) to (TEMP-15):

Substituted Aryl Group (Set of Specific Examples G1B):

an o-tolyl group,

a m-tolyl group,

a p-tolyl group,

a p-xylyl group,

a m-xylyl group,

an o-xylyl group,

a p-isopropylphenyl group,

a m-isopropylphenyl group,

an o-isopropylphenyl group,

a p-t-butylphenyl group,

a m-t-butylphenyl group,

a o-t-butylphenyl group,

a 3,4,5-trimethylphenyl group,

a 9,9-dimethylfluorenyl group,

a 9,9-diphenylfluorenyl group,

a 9,9-bis(4-methylphenyl)fluorenyl group,

a 9,9-bis(4-isopropylphenyl)fluorenyl group,

a 9,9-bis(4-t-butylphenyl)fluorenyl group,

a cyanophenyl group,

a triphenylsilylphenyl group,

a trimethylsilylphenyl group,

a phenylnaphthyl group,

a naphthylphenyl group, and

groups formed by substituting one or more hydrogen atom of each ofmonovalent aryl groups derived from the ring structures represented bythe general formulae (TEMP-1) to (TEMP-15) by a substituent.

Substituted or Unsubstituted Heterocyclic Group

In the description herein, the “heterocyclic group” means a cyclic groupcontaining at least one hetero atom in the ring atoms. Specific examplesof the hetero atom include a nitrogen atom, an oxygen atom, a sulfuratom, a silicon atom, a phosphorus atom, and a boron atom.

In the description herein, the “heterocyclic group” is a monocyclicgroup or a condensed ring group.

In the description herein, the “heterocyclic group” is an aromaticheterocyclic group or a non-aromatic heterocyclic group.

In the description herein, specific examples (set of specific examplesG2) of the “substituted or unsubstituted heterocyclic group” include theunsubstituted heterocyclic groups (set of specific examples G2A) and thesubstituted heterocyclic groups (set of specific examples G2B) shownbelow. (Herein, the unsubstituted heterocyclic group means the casewhere the “substituted or unsubstituted heterocyclic group” is an“unsubstituted heterocyclic group”, and the substituted heterocyclicgroup means the case where the “substituted or unsubstitutedheterocyclic group” is a “substituted heterocyclic group”.) In thedescription herein, the simple expression “heterocyclic group”encompasses both the “unsubstituted heterocyclic group” and the“substituted heterocyclic group”.

The “substituted heterocyclic group” means a group formed bysubstituting one or more hydrogen atom of the “unsubstitutedheterocyclic group” by a substituent. Specific examples of the“substituted heterocyclic group” include groups formed by substituting ahydrogen atom of each of the “unsubstituted heterocyclic groups” in theset of specific examples G2A by a substituent, and the examples of thesubstituted heterocyclic groups in the set of specific examples G2B. Theexamples of the “unsubstituted heterocyclic group” and the examples ofthe “substituted heterocyclic group” enumerated herein are mereexamples, and the “substituted heterocyclic group” in the descriptionherein encompasses groups formed by substituting a hydrogen atom bondedto the ring atom of the heterocyclic group itself of each of the“substituted heterocyclic groups” in the set of specific examples G2B bya substituent, and groups formed by substituting a hydrogen atom of thesubstituent of each of the “substituted heterocyclic groups” in the setof specific examples G2B by a substituent.

The set of specific examples G2A includes, for example, theunsubstituted heterocyclic group containing a nitrogen atom (set ofspecific examples G2A1), the unsubstituted heterocyclic group containingan oxygen atom (set of specific examples G2A2), the unsubstitutedheterocyclic group containing a sulfur atom (set of specific examplesG2A3), and monovalent heterocyclic groups derived by removing onehydrogen atom from each of the ring structures represented by thefollowing general formulae (TEMP-16) to (TEMP-33) (set of specificexamples G2A4).

The set of specific examples G2B includes, for example, the substitutedheterocyclic groups containing a nitrogen atom (set of specific examplesG2B1), the substituted heterocyclic groups containing an oxygen atom(set of specific examples G2B2), the substituted heterocyclic groupscontaining a sulfur atom (set of specific examples G2B3), and groupsformed by substituting one or more hydrogen atom of each of monovalentheterocyclic groups derived from the ring structures represented by thefollowing general formulae (TEMP-16) to (TEMP-33) by a substituent (setof specific examples G2B4).

Unsubstituted Heterocyclic Group Containing Nitrogen Atom (Set ofSpecific Examples G2A1):

a pyrrolyl group,

an imidazolyl group,

a pyrazolyl group,

a triazolyl group,

a tetrazolyl group,

an oxazolyl group,

an isoxazolyl group,

an oxadiazolyl group,

a thiazolyl group,

an isothiazolyl group,

a thiadiazolyl group,

a pyridyl group,

a pyridazinyl group,

a pyrimidinyl group,

a pyrazinyl group,

a triazinyl group,

an indolyl group,

an isoindolyl group,

an indolizinyl group,

a quinolizinyl group,

a quinolyl group,

an isoquinolyl group,

a cinnolinyl group,

a phthalazinyl group,

a quinazolinyl group,

a quinoxalinyl group,

a benzimidazolyl group,

an indazolyl group,

a phenanthrolinyl group,

a phenanthridinyl group,

an acridinyl group,

a phenazinyl group,

a carbazolyl group,

a benzocarbazolyl group,

a morpholino group,

a phenoxazinyl group,

a phenothiazinyl group,

an azacarbazolyl group, and

a diazacarbazolyl group.

Unsubstituted Heterocyclic Group containing Oxygen Atom (Set of SpecificExamples G2A2):

a furyl group,

an oxazolyl group,

an isoxazolyl group,

an oxadiazolyl group,

a xanthenyl group,

a benzofuranyl group,

an isobenzofuranyl group,

a dibenzofuranyl group,

a naphthobenzofuranyl group,

a benzoxazolyl group,

a benzisoxazolyl group,

a phenoxazinyl group,

a morpholino group,

a dinaphthofuranyl group,

an azadibenzofuranyl group,

a diazadibenzofuranyl group,

an azanaphthobenzofuranyl group, and

a diazanaphthobenzofuranyl group.

Unsubstituted Heterocyclic Group Containing Sulfur Atom (Set of SpecificExamples G2A3):

a thienyl group,

a thiazolyl group,

an isothiazolyl group,

a thiadiazolyl group,

a benzothiophenyl group (benzothienyl group),

an isobenzothiophenyl group (isobenzothienyl group),

a dibenzothiophenyl group (dibenzothienyl group),

a naphthobenzothiophenyl group (naphthobenzothienyl group),

a benzothiazolyl group,

a benzisothiazolyl group,

a phenothiazinyl group,

a dinaphthothiophenyl group (dinaphthothienyl group),

an azadibenzothiophenyl group (azadibenzothienyl group),

a diazadibenzothiophenyl group (diazadibenzothienyl group),

an azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and

a diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

Monovalent Heterocyclic Group Derived by Removing One Hydrogen Atom fromRing Structures represented by General Formulae (TEMP-16) to (TEMP-33)(Set of Specific Examples G2A4)

In the general formulae (TEMP-16) to (TEMP-33), X_(A) and Y_(A) eachindependently represent an oxygen atom, a sulfur atom, NH, or CH₂,provided that at least one of X_(A) and Y_(A) represents an oxygen atom,a sulfur atom, or NH.

In the general formulae (TEMP-16) to (TEMP-33), in the case where atleast one of X_(A) and Y_(A) represents NH or CH₂, the monovalentheterocyclic groups derived from the ring structures represented by thegeneral formulae (TEMP-16) to (TEMP-33) include monovalent groups formedby removing one hydrogen atom from the NH or CH₂.

Substituted Heterocyclic Group Containing Nitrogen Atom (Set of SpecificExamples G2B1):

a (9-phenyl)carbazolyl group,

a (9-biphenylyl)carbazolyl group,

a (9-phenyl)phenylcarbazolyl group,

a (9-naphthyl)carbazolyl group,

a diphenylcarbazol-9-yl group,

a phenylcarbazol-9-yl group,

a methylbenzimidazolyl group,

an ethylbenzimidazolyl group,

a phenyltriazinyl group,

a biphenyltriazinyl group,

a diphenyltriazinyl group,

a phenylquinazolinyl group, and

a biphenylquinazolinyl group.

Substituted Heterocyclic Group Containing Oxygen Atom (Set of SpecificExamples G2B2):

a phenyldibenzofuranyl group,

a methyldibenzofuranyl group,

a t-butyldibenzofuranyl group, and

a monovalent residual group of spiro[9H-xanthene-9,9′-[9H]fluorene].

Substituted Heterocyclic Group containing Sulfur Atom (Set of SpecificExamples G2B3):

a phenyldibenzothiophenyl group,

a methyldibenzothiophenyl group,

a t-butyldibenzothiophenyl group, and

a monovalent residual group of spiro[9H-thioxanthene-9,9′-[9H]fluorene].

Group formed by substituting one or more Hydrogen Atom of MonovalentHeterocyclic Group derived from Ring Structures represented by GeneralFormulae (TEMP-16) to (TEMP-33) by Substituent (Set of Specific ExamplesG2B4)

The “one or more hydrogen atom of the monovalent heterocyclic group”means one or more hydrogen atom selected from the hydrogen atom bondedto the ring carbon atom of the monovalent heterocyclic group, thehydrogen atom bonded to the nitrogen atom in the case where at least oneof X_(A) and Y_(A) represents NH, and the hydrogen atom of the methylenegroup in the case where one of X_(A) and Y_(A)represents CH₂.

Substituted or Unsubstituted Alkyl Group

In the description herein, specific examples (set of specific examplesG3) of the “substituted or unsubstituted alkyl group” include theunsubstituted alkyl groups (set of specific examples G3A) and thesubstituted alkyl groups (set of specific examples G3B) shown below.(Herein, the unsubstituted alkyl group means the case where the“substituted or unsubstituted alkyl group” is an “unsubstituted alkylgroup”, and the substituted alkyl group means the case where the“substituted or unsubstituted alkyl group” is a “substituted alkylgroup”.) In the description herein, the simple expression “alkyl group”encompasses both the “unsubstituted alkyl group” and the “substitutedalkyl group”.

The “substituted alkyl group” means a group formed by substituting oneor more hydrogen atom of the “unsubstituted alkyl group” by asubstituent. Specific examples of the “substituted alkyl group” includegroups formed by substituting one or more hydrogen atom of each of the“unsubstituted alkyl groups” (set of specific examples G3A) by asubstituent, and the examples of the substituted alkyl groups (set ofspecific examples G3B). In the description herein, the alkyl group inthe “unsubstituted alkyl group” means a chain-like alkyl group.Accordingly, the “unsubstituted alkyl group” encompasses an“unsubstituted linear alkyl group” and an “unsubstituted branched alkylgroup”. The examples of the “unsubstituted alkyl group” and the examplesof the “substituted alkyl group” enumerated herein are mere examples,and the “substituted alkyl group” in the description herein encompassesgroups formed by substituting a hydrogen atom of the alkyl group itselfof each of the “substituted alkyl groups” in the set of specificexamples G3B by a substituent, and groups formed by substituting ahydrogen atom of the substituent of each of the “substituted alkylgroups” in the set of specific examples G3B by a substituent.

Unsubstituted Alkyl Group (Set of Specific Examples G3A):

a methyl group,

an ethyl group,

a n-propyl group,

an isopropyl group,

a n-butyl group,

an isobutyl group,

a s-butyl group, and

a t-butyl group.

Substituted Alkyl Group (Set of Specific Examples G3B):

a heptafluoropropyl group (including isomers),

a pentafluoroethyl group,

a 2,2,2-trifluoroethyl group, and

a trifluoromethyl group.

Substituted or Unsubstituted Alkenyl Group

In the description herein, specific examples (set of specific examplesG4) of the “substituted or unsubstituted alkenyl group” include theunsubstituted alkenyl groups (set of specific examples G4A) and thesubstituted alkenyl groups (set of specific examples G4B) shown below.(Herein, the unsubstituted alkenyl group means the case where the“substituted or unsubstituted alkenyl group” is an “unsubstitutedalkenyl group”, and the substituted alkenyl group means the case wherethe “substituted or unsubstituted alkenyl group” is a “substitutedalkenyl group”.) In the description herein, the simple expression“alkenyl group” encompasses both the “unsubstituted alkenyl group” andthe “substituted alkenyl group”.

The “substituted alkenyl group” means a group formed by substituting oneor more hydrogen atom of the “unsubstituted alkenyl group” by asubstituent. Specific examples of the “substituted alkenyl group”include the “unsubstituted alkenyl groups” (set of specific examplesG4A) that each have a substituent, and the examples of the substitutedalkenyl groups (set of specific examples G4B). The examples of the“unsubstituted alkenyl group” and the examples of the “substitutedalkenyl group” enumerated herein are mere examples, and the “substitutedalkenyl group” in the description herein encompasses groups formed bysubstituting a hydrogen atom of the alkenyl group itself of each of the“substituted alkenyl groups” in the set of specific examples G4B by asubstituent, and groups formed by substituting a hydrogen atom of thesubstituent of each of the “substituted alkenyl groups” in the set ofspecific examples G4B by a substituent.

Unsubstituted Alkenyl Group (Set of Specific Examples G4A):

a vinyl group,

an allyl group,

a 1-butenyl group,

a 2-butenyl group, and

a 3-butenyl group.

Substituted Alkenyl Group (Set of Specific Examples G4B):

a 1,3-butanedienyl group,

a 1-methylvinyl group,

a 1-methylallyl group,

a 1,1-dimethylallyl group,

a 2-methylallyl group, and

a 1,2-dimethylallyl group.

Substituted or Unsubstituted Alkynyl Group

In the description herein, specific examples (set of specific examplesG5) of the “substituted or unsubstituted alkynyl group” include theunsubstituted alkynyl group (set of specific examples G5A) shown below.(Herein, the unsubstituted alkynyl group means the case where the“substituted or unsubstituted alkynyl group” is an “unsubstitutedalkynyl group”.) In the description herein, the simple expression“alkynyl group” encompasses both the “unsubstituted alkynyl group” andthe “substituted alkynyl group”.

The “substituted alkynyl group” means a group formed by substituting oneor more hydrogen atom of the “unsubstituted alkynyl group” by asubstituent. Specific examples of the “substituted alkenyl group”include groups formed by substituting one or more hydrogen atom of the“unsubstituted alkynyl group” (set of specific examples G5A) by asubstituent.

Unsubstituted Alkynyl Group (Set of Specific Examples G5A):

an ethynyl group.

Substituted or Unsubstituted Cycloalkyl Group

In the description herein, specific examples (set of specific examplesG6) of the “substituted or unsubstituted cycloalkyl group” include theunsubstituted cycloalkyl groups (set of specific examples G6A) and thesubstituted cycloalkyl group (set of specific examples G6B) shown below.(Herein, the unsubstituted cycloalkyl group means the case where the“substituted or unsubstituted cycloalkyl group” is an “unsubstitutedcycloalkyl group”, and the substituted cycloalkyl group means the casewhere the “substituted or unsubstituted cycloalkyl group” is a“substituted cycloalkyl group”.) In the description herein, the simpleexpression “cycloalkyl group” encompasses both the “unsubstitutedcycloalkyl group” and the “substituted cycloalkyl group”.

The “substituted cycloalkyl group” means a group formed by substitutingone or more hydrogen atom of the “unsubstituted cycloalkyl group” by asubstituent. Specific examples of the “substituted cycloalkyl group”include groups formed by substituting one or more hydrogen atom of eachof the “unsubstituted cycloalkyl groups” (set of specific examples G6A)by a substituent, and the example of the substituted cycloalkyl group(set of specific examples G6B). The examples of the “unsubstitutedcycloalkyl group” and the examples of the “substituted cycloalkyl group”enumerated herein are mere examples, and the “substituted cycloalkylgroup” in the description herein encompasses groups formed bysubstituting one or more hydrogen atom bonded to the carbon atoms of thecycloalkyl group itself of the “substituted cycloalkyl group” in the setof specific examples G6B by a substituent, and groups formed bysubstituting a hydrogen atom of the substituent of the “substitutedcycloalkyl group” in the set of specific examples G6B by a substituent.

Unsubstituted Cycloalkyl Group (Set of Specific Examples G6A):

a cyclopropyl group,

a cyclobutyl group,

a cyclopentyl group,

a cyclohexyl group,

a 1-adamantyl group,

a 2-adamantyl group,

a 1-norbornyl group, and

a 2-norbornyl group.

Substituted Cycloalkyl Group (Set of Specific Examples G6B):

a 4-methylcyclohexyl group.

Group represented by —Si(R₉₀₁)(R₉₀₂)(R₉₀₃)

In the description herein, specific examples (set of specific examplesG7) of the group represented by —Si(R₉₀₁)(R₉₀₂)(R₉₀₃) include:

—Si(G1)(G1)(G1),

—Si(G1)(G2)(G2),

—Si(G1)(G1)(G2),

—Si(G2)(G2)(G2),

—Si(G3)(G3)(G3), and

—Si(G6)(G6)(G6).

Herein,

G1 represents the “substituted or unsubstituted aryl group” described inthe set of specific examples G1,

G2 represents the “substituted or unsubstituted heterocyclic group”described in the set of specific examples G2,

G3 represents the “substituted or unsubstituted alkyl group” describedin the set of specific examples G3, and

G6 represents the “substituted or unsubstituted cycloalkyl group”described in the set of specific examples G6.

Plural groups represented by G1 in —Si(G1)(G1)(G1) are the same as ordifferent from each other.

Plural groups represented by G2 in —Si(G1)(G2)(G2) are the same as ordifferent from each other.

Plural groups represented by G1 in —Si(G1)(G1)(G2) are the same as ordifferent from each other.

Plural groups represented by G2 in —Si(G2)(G2)(G2) are the same as ordifferent from each other.

Plural groups represented by G3 in —Si(G3)(G3)(G3) are the same as ordifferent from each other.

Plural groups represented by G6 in —Si(G6)(G6)(G6) are the same as ordifferent from each other.

Group represented by —O—(R₉₀₄)

In the description herein, specific examples (set of specific examplesG8) of the group represented by —O—(R₉₀₄) include:

—O(G1),

—O(G2),

—O(G3), and

—O(G6).

Herein,

G1 represents the “substituted or unsubstituted aryl group” described inthe set of specific examples G1,

G2 represents the “substituted or unsubstituted heterocyclic group”described in the set of specific examples G2,

G3 represents the “substituted or unsubstituted alkyl group” describedin the set of specific examples G3, and

G6 represents the “substituted or unsubstituted cycloalkyl group”described in the set of specific examples G6.

Group Represented by —S—(R₉₀₅)

In the description herein, specific examples (set of specific examplesG9) of the group represented by —S—(R₉₀₅) include:

—S(G1),

—S(G2),

—S(G3), and

—S(G6).

Herein,

G1 represents the “substituted or unsubstituted aryl group” described inthe set of specific examples G1,

G2 represents the “substituted or unsubstituted heterocyclic group”described in the set of specific examples G2,

G3 represents the “substituted or unsubstituted alkyl group” describedin the set of specific examples G3, and

G6 represents the “substituted or unsubstituted cycloalkyl group”described in the set of specific examples G6.

Group Represented by —N(R₉₀₆)(R₉₀₇)

In the description herein, specific examples (set of specific examplesG10) of the group represented by —N(R₉₀₆)(R₉₀₇) include:

—N(G1)(G1),

—N(G2)(G2),

—N(G1)(G2),

—N(G3)(G3), and

—N(G6)(G6).

G1 represents the “substituted or unsubstituted aryl group” described inthe set of specific examples G1,

G2 represents the “substituted or unsubstituted heterocyclic group”described in the set of specific examples G2,

G3 represents the “substituted or unsubstituted alkyl group” describedin the set of specific examples G3, and

G6 represents the “substituted or unsubstituted cycloalkyl group”described in the set of specific examples G6.

Plural groups represented by G1 in —N(G1)(G1) are the same as ordifferent from each other.

Plural groups represented by G2 in —N(G2)(G2) are the same as ordifferent from each other.

Plural groups represented by G3 in —N(G3)(G3) are the same as ordifferent from each other.

Plural groups represented by G6 in —N(G6)(G6) are the same as ordifferent from each other.

Halogen Atom

In the description herein, specific examples (set of specific examplesG11) of the “halogen atom” include a fluorine atom, a chlorine atom, abromine atom, and an iodine atom.

Substituted or Unsubstituted Fluoroalkyl Group

In the description herein, the “substituted or unsubstituted fluoroalkylgroup” means a group formed by substituting at least one hydrogen atombonded to the carbon atom constituting the alkyl group in the“substituted or unsubstituted alkyl group” by a fluorine atom, andencompasses a group formed by substituting all the hydrogen atoms bondedto the carbon atoms constituting the alkyl group in the “substituted orunsubstituted alkyl group” by fluorine atoms (i.e., a perfluoroalkylgroup). The number of carbon atoms of the “unsubstituted fluoroalkylgroup” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18,unless otherwise indicated in the description. The “substitutedfluoroalkyl group” means a group formed by substituting one or morehydrogen atom of the “fluoroalkyl group” by a substituent. In thedescription herein, the “substituted fluoroalkyl group” encompasses agroup formed by substituting one or more hydrogen atom bonded to thecarbon atom of the alkyl chain in the “substituted fluoroalkyl group” bya substituent, and a group formed by substituting one or more hydrogenatom of the substituent in the “substituted fluoroalkyl group” by asubstituent. Specific examples of the “unsubstituted fluoroalkyl group”include examples of groups formed by substituting one or more hydrogenatom in each of the “alkyl group” (set of specific examples G3) by afluorine atom.

Substituted or Unsubstituted Haloalkyl Group

In the description herein, the “substituted or unsubstituted haloalkylgroup” means a group formed by substituting at least one hydrogen atombonded to the carbon atom constituting the alkyl group in the“substituted or unsubstituted alkyl group” by a halogen atom, andencompasses a group formed by substituting all the hydrogen atoms bondedto the carbon atoms constituting the alkyl group in the “substituted orunsubstituted alkyl group” by halogen atoms. The number of carbon atomsof the “unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30,and more preferably 1 to 18, unless otherwise indicated in thedescription. The “substituted haloalkyl group” means a group formed bysubstituting one or more hydrogen atom of the “haloalkyl group” by asubstituent. In the description herein, the “substituted haloalkylgroup” encompasses a group formed by substituting one or more hydrogenatom bonded to the carbon atom of the alkyl chain in the “substitutedhaloalkyl group” by a substituent, and a group formed by substitutingone or more hydrogen atom of the substituent in the “substitutedhaloalkyl group” by a substituent. Specific examples of the“unsubstituted haloalkyl group” include examples of groups formed bysubstituting one or more hydrogen atom in each of the “alkyl group” (setof specific examples G3) by a halogen atom. A haloalkyl group may bereferred to as a halogenated alkyl group in some cases.

Substituted or Unsubstituted Alkoxy Group

In the description herein, specific examples of the “substituted orunsubstituted alkoxy group” include a group represented by —O(G3),wherein G3 represents the “substituted or unsubstituted alkyl group”described in the set of specific examples G3. The number of carbon atomsof the “unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, andmore preferably 1 to 18, unless otherwise indicated in the description.

Substituted or Unsubstituted Alkylthio Group

In the description herein, specific examples of the “substituted orunsubstituted alkylthio group” include a group represented by —S(G3),wherein G3 represents the “substituted or unsubstituted alkyl group”described in the set of specific examples G3. The number of carbon atomsof the “unsubstituted alkylthio group” is 1 to 50, preferably 1 to 30,and more preferably 1 to 18, unless otherwise indicated in thedescription.

Substituted or Unsubstituted Aryloxy Group

In the description herein, specific examples of the “substituted orunsubstituted aryloxy group” include a group represented by —O(G1),wherein G1 represents the “substituted or unsubstituted aryl group”described in the set of specific examples G1. The number of ring carbonatoms of the “unsubstituted aryloxy group” is 6 to 50, preferably 6 to30, and more preferably 6 to 18, unless otherwise indicated in thedescription.

Substituted or Unsubstituted Arylthio Group

In the description herein, specific examples of the “substituted orunsubstituted arylthio group” include a group represented by —S(G1),wherein G1 represents the “substituted or unsubstituted aryl group”described in the set of specific examples G1. The number of ring carbonatoms of the “unsubstituted arylthio group” is 6 to 50, preferably 6 to30, and more preferably 6 to 18, unless otherwise indicated in thedescription.

Substituted or Unsubstituted Trialkylsilyl Group

In the description herein, specific examples of the “trialkylsilylgroup” include a group represented by —Si(G3)(G3)(G3), wherein G3represents the “substituted or unsubstituted alkyl group” described inthe set of specific examples G3. Plural groups represented by G3 in—Si(G3)(G3)(G3) are the same as or different from each other. The numberof carbon atoms of each of alkyl groups of the “substituted orunsubstituted trialkylsilyl group” is 1 to 50, preferably 1 to 20, andmore preferably 1 to 6, unless otherwise indicated in the description.

Substituted or Unsubstituted Aralkyl Group

In the description herein, specific examples of the “substituted orunsubstituted aralkyl group” include a group represented by -(G3)-(G1),wherein G3 represents the “substituted or unsubstituted alkyl group”described in the set of specific examples G3, and G1 represents the“substituted or unsubstituted aryl group” described in the set ofspecific examples G1. Accordingly, the “aralkyl group” is a group formedby substituting a hydrogen atom of an “alkyl group” by an “aryl group”as a substituent, and is one embodiment of the “substituted alkylgroup”. The “unsubstituted aralkyl group” is an “unsubstituted alkylgroup” that is substituted by an “unsubstituted aryl group”, and thenumber of carbon atoms of the “unsubstituted aralkyl group” is 7 to 50,preferably 7 to 30, and more preferably 7 to 18, unless otherwiseindicated in the description.

Specific examples of the “substituted or unsubstituted aralkyl group”include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butylgroup, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a2-α-naphthylisopropyl group, a ß-naphthylmethyl group, a1-ß-naphthylethyl group, a 2-ß-naphthylethyl group, a1-ß-naphthylisopropyl group, and a 2-ß-naphthylisopropyl group.

In the description herein, the substituted or unsubstituted aryl groupis preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, ano-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, ap-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-ylgroup, a m-terphenyl-2-yl group, an o-terphenyl-4-yl group, ano-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenylgroup, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a9,9′-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a9,9-diphenylfluorenyl group, and the like, unless otherwise indicated inthe description.

In the description herein, the substituted or unsubstituted heterocyclicgroup is preferably a pyridyl group, a pyrimidinyl group, a triazinylgroup, a quinolyl group, an isoquinolyl group, a quinazolinyl group, abenzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (e.g.,a 1-carbazolyl, group, a 2-carbazolyl, group, a 3-carbazolyl, group, a4-carbazolyl, group, or a 9-carbazolyl, group), a benzocarbazolyl group,an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group,a naphthobenzofuranly group, an azadibenzofuranyl group, adiazadibenzofuranyl group, a dibenzothiophenyl group, anaphthobenzothiophenyl group, an azadibenzothiophenyl group, adiazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (e.g., a(9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a(9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a(9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, adiphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, aphenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinylgroup, a phenyldibenzofuranyl group, a phenyldibenzothiophenyl group,and the like, unless otherwise indicated in the description.

In the description herein, the carbazolyl group is specifically any oneof the following groups unless otherwise indicated in the description.

In the description herein, the (9-phenyl)carbazolyl group isspecifically any one of the following groups unless otherwise indicatedin the description.

In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bondingsite.

In the description herein, the dibenzofuranyl group and thedibenzothiophenyl group are specifically any one of the following groupsunless otherwise indicated in the description.

In the general formulae (TEMP-34) to (TEMP-41), * represents a bondingsite.

In the description herein, the substituted or unsubstituted alkyl groupis preferably a methyl group, an ethyl group, a propyl group, anisopropyl group, a n-butyl group, an isobutyl group, a t-butyl group, orthe like unless otherwise indicated in the description.

Substituted or Unsubstituted Arylene Group

In the description herein, the “substituted or unsubstituted arylenegroup” is a divalent group derived by removing one hydrogen atom on thearyl ring from the “substituted or unsubstituted aryl group” describedabove unless otherwise indicated in the description. Specific examples(set of specific examples G12) of the “substituted or unsubstitutedarylene group” include divalent groups derived by removing one hydrogenatom on the aryl ring from the “substituted or unsubstituted arylgroups” described in the set of specific examples G1.

Substituted or Unsubstituted Divalent Heterocyclic Group

In the description herein, the “substituted or unsubstituted divalentheterocyclic group” is a divalent group derived by removing one hydrogenatom on the heterocyclic ring from the “substituted or unsubstitutedheterocyclic group” described above unless otherwise indicated in thedescription. Specific examples (set of specific examples G13) of the“substituted or unsubstituted divalent heterocyclic group” includedivalent groups derived by removing one hydrogen atom on theheterocyclic ring from the “substituted or unsubstituted heterocyclicgroups” described in the set of specific examples G2.

Substituted or Unsubstituted Alkylene Group

In the description herein, the “substituted or unsubstituted alkylenegroup” is a divalent group derived by removing one hydrogen atom on thealkyl chain from the “substituted or unsubstituted alkyl group”described above unless otherwise indicated in the description. Specificexamples (set of specific examples G14) of the “substituted orunsubstituted alkylene group” include divalent groups derived byremoving one hydrogen atom on the alkyl chain from the “substituted orunsubstituted alkyl groups” described in the set of specific examplesG3.

In the description herein, the substituted or unsubstituted arylenegroup is preferably any one of the groups represented by the followinggeneral formulae (TEMP-42) to (TEMP-68) unless otherwise indicated inthe description.

In the general formulae (TEMP-42) to (TEMP-52), Q₁ to Q₁₀ eachindependently represent a hydrogen atom or a substituent.

In the general formulae (TEMP-42) to (TEMP-52), * represents a bondingsite.

In the general formulae (TEMP-53) to (TEMP-62), Q₁ to Q₁₀ eachindependently represent a hydrogen atom or a substituent.

The formulae Q₉ and Q₁₀ may be bonded to each other to form a ring via asingle bond.

In the general formulae (TEMP-53) to (TEMP-62), * represents a bondingsite.

In the general formulae (TEMP-63) to (TEMP-68), Q₁ to Q₈ eachindependently represent a hydrogen atom or a substituent.

In the general formulae (TEMP-63) to (TEMP-68), * represents a bondingsite.

In the description herein, the substituted or unsubstituted divalentheterocyclic group is preferably the groups represented by the followinggeneral formulae (TEMP-69) to (TEMP-102) unless otherwise indicated inthe description.

In the general formulae (TEMP-69) to (TEMP-82), Q₁ to Q₈ eachindependently represent a hydrogen atom or a substituent.

In the general formulae (TEMP-83) to (TEMP-102), Q₁ to Q₈ eachindependently represent a hydrogen atom or a substituent.

The above are the explanation of the “substituents in the descriptionherein”.

Case Forming Ring by Bonding

In the description herein, the case where “one or more combinations ofcombinations each including adjacent two or more each are bonded to eachother to form a substituted or unsubstituted monocyclic ring, or eachare bonded to each other to form a substituted or unsubstitutedcondensed ring, or each are not bonded to each other” means a case where“one or more combinations of combinations each including adjacent two ormore each are bonded to each other to form a substituted orunsubstituted monocyclic ring”, a case where “one or more combinationsof combinations each including adjacent two or more each are bonded toeach other to form a substituted or unsubstituted condensed ring”, and acase where “one or more combinations of combinations each includingadjacent two or more each are not bonded to each other”.

In the description herein, the case where “one or more combinations ofcombinations each including adjacent two or more each are bonded to eachother to form a substituted or unsubstituted monocyclic ring” and thecase where “one or more combinations of combinations each includingadjacent two or more each are bonded to each other to form a substitutedor unsubstituted condensed ring” (which may be hereinafter collectivelyreferred to as a “case forming a ring by bonding”) will be explainedbelow. The cases will be explained for the anthracene compoundrepresented by the following general formula (TEMP-103) having ananthracene core skeleton as an example.

For example, in the case where “one or more combinations of combinationseach including adjacent two or more each are bonded to each other toform a ring” among R₉₂₁ to R₉₃₀, the combinations each includingadjacent two as one combination include a combination of R₉₂₁ and R₉₂₂,a combination of R₉₂₂ and R₉₂₃, a combination of R₉₂₃ and R₉₂₄, acombination of R₉₂₄ and R₉₃₀, a combination of R₉₃₀ and R₉₂₅, acombination of R₉₂₅ and R₉₂₆, a combination of R₉₂₆ and R₉₂₇, acombination of R₉₂₇ and R₉₂₈, a combination of R₉₂₈ and R₉₂₉, and acombination of R₉₂₉ and R₉₂₁.

The “one or more combinations” mean that two or more combinations eachincluding adjacent two or more may form rings simultaneously. Forexample, in the case where R₉₂₁ and R₉₂₂ are bonded to each other toform a ring Q_(A), and simultaneously R₉₂₅ and R₉₂₆ are bonded to eachother to form a ring Q_(B), the anthracene compound represented by thegeneral formula (TEMP-103) is represented by the following generalformula (TEMP-104).

The case where the “combination including adjacent two or more formsrings” encompasses not only the case where adjacent two included in thecombination are bonded as in the aforementioned example, but also thecase where adjacent three or more included in the combination arebonded. For example, this case means that R₉₂₁ and R₉₂₂ are bonded toeach other to form a ring Q_(A), R₉₂₂ and R₉₂₃ are bonded to each otherto form a ring Q_(C), and adjacent three (R₉₂₁, R₉₂₂, and R₉₂₃) includedin the combination are bonded to each other to form rings, which arecondensed to the anthracene core skeleton, and in this case, theanthracene compound represented by the general formula (TEMP-103) isrepresented by the following general formula (TEMP-105). In thefollowing general formula (TEMP-105), the ring Q_(A) and the ring Q_(C)share R₉₂₂.

The formed “monocyclic ring” or “condensed ring” may be a saturated ringor an unsaturated ring in terms of structure of the formed ring itself.In the case where the “one combination including adjacent two” forms a“monocyclic ring” or a “condensed ring”, the “monocyclic ring” or the“condensed ring” may form a saturated ring or an unsaturated ring. Forexample, the ring Q_(A) and the ring Q_(B) formed in the general formula(TEMP-104) each are a “monocyclic ring” or a “condensed ring”. The ringQ_(A) and the ring Q_(C) formed in the general formula (TEMP-105) eachare a “condensed ring”. The ring Q_(A) and the ring Q_(C) in the generalformula (TEMP-105) form a condensed ring through condensation of thering Q_(A) and the ring Q_(C). In the case where the ring Q_(A) in thegeneral formula (TMEP-104) is a benzene ring, the ring Q_(A) is amonocyclic ring. In the case where the ring Q_(A) in the general formula(TMEP-104) is a naphthalene ring, the ring Q_(A) is a condensed ring.

The “unsaturated ring” means an aromatic hydrocarbon ring or an aromaticheterocyclic ring. The “saturated ring” means an aliphatic hydrocarbonring or a non-aromatic heterocyclic ring.

Specific examples of the aromatic hydrocarbon ring include thestructures formed by terminating the groups exemplified as the specificexamples in the set of specific examples G1 with a hydrogen atom.

Specific examples of the aromatic heterocyclic ring include thestructures formed by terminating the aromatic heterocyclic groupsexemplified as the specific examples in the set of specific examples G2with a hydrogen atom.

Specific examples of the aliphatic hydrocarbon ring include thestructures formed by terminating the groups exemplified as the specificexamples in the set of specific examples G6 with a hydrogen atom.

The expression “to form a ring” means that the ring is formed only withthe plural atoms of the core structure or with the plural atoms of thecore structure and one or more arbitrary element. For example, the ringQ_(A) formed by bonding R₉₂₁ and R₉₂₂ each other shown in the generalformula (TEMP-104) means a ring formed with the carbon atom of theanthracene skeleton bonded to R₉₂₁, the carbon atom of the anthraceneskeleton bonded to R₉₂₂, and one or more arbitrary element. As aspecific example, in the case where the ring Q_(A) is formed with R₉₂₁and R₉₂₂, and in the case where a monocyclic unsaturated ring is formedwith the carbon atom of the anthracene skeleton bonded to R₉₂₁, thecarbon atom of the anthracene skeleton bonded to R₉₂₂, and four carbonatoms, the ring formed with R₉₂₁ and R₉₂₂ is a benzene ring.

Herein, the “arbitrary element” is preferably at least one kind of anelement selected from the group consisting of a carbon element, anitrogen element, an oxygen element, and a sulfur element, unlessotherwise indicated in the description. For the arbitrary element (forexample, for a carbon element or a nitrogen element), a bond that doesnot form a ring may be terminated with a hydrogen atom or the like, andmay be substituted by an “arbitrary substituent” described later. In thecase where an arbitrary element other than a carbon element iscontained, the formed ring is a heterocyclic ring.

The number of the “one or more arbitrary element” constituting themonocyclic ring or the condensed ring is preferably 2 or more and 15 orless, more preferably 3 or more and 12 or less, and further preferably 3or more and 5 or less, unless otherwise indicated in the description.

What is preferred between the “monocyclic ring” and the “condensed ring”is the “monocyclic ring” unless otherwise indicated in the description.

What is preferred between the “saturated ring” and the “unsaturatedring” is the “unsaturated ring” unless otherwise indicated in thedescription.

The “monocyclic ring” is preferably a benzene ring unless otherwiseindicated in the description.

The “unsaturated ring” is preferably a benzene ring unless otherwiseindicated in the description.

In the case where the “one or more combinations of combinations eachincluding adjacent two or more” each are “bonded to each other to form asubstituted or unsubstituted monocyclic ring”, or each are “bonded toeach other to form a substituted or unsubstituted condensed ring”, it ispreferred that the one or more combinations of combinations eachincluding adjacent two or more each are bonded to each other to form asubstituted or unsubstituted “unsaturated ring” containing the pluralatoms of the core skeleton and 1 or more and 15 or less at least onekind of an element selected from the group consisting of a carbonelement, a nitrogen element, an oxygen element, and a sulfur element,unless otherwise indicated in the description.

In the case where the “monocyclic ring” or the “condensed ring” has asubstituent, the substituent is, for example, an “arbitrary substituent”described later. In the case where the “monocyclic ring” or the“condensed ring” has a substituent, specific examples of the substituentinclude the substituents explained in the section “Substituents inDescription” described above.

In the case where the “saturated ring” or the “unsaturated ring” has asubstituent, the substituent is, for example, an “arbitrary substituent”described later. In the case where the “monocyclic ring” or the“condensed ring” has a substituent, specific examples of the substituentinclude the substituents explained in the section “Substituents inDescription” described above.

The above are the explanation of the case where “one or morecombinations of combinations each including adjacent two or more” eachare “bonded to each other to form a substituted or unsubstitutedmonocyclic ring”, and the case where “one or more combinations ofcombinations each including adjacent two or more” each are “bonded toeach other to form a substituted or unsubstituted condensed ring” (i.e.,the “case forming a ring by bonding”).

Substituent for “Substituted or Unsubstituted”

In one embodiment in the description herein, the substituent for thecase of “substituted or unsubstituted” (which may be hereinafterreferred to as an “arbitrary substituent”) is, for example, a groupselected from the group consisting of

an unsubstituted alkyl group having 1 to 50 carbon atoms,

an unsubstituted alkenyl group having 2 to 50 carbon atoms,

an unsubstituted alkynyl group having 2 to 50 carbon atoms,

an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄),

—S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),

a halogen atom, a cyano group, a nitro group,

an unsubstituted aryl group having 6 to 50 ring carbon atoms, and

an unsubstituted heterocyclic group having 5 to 50 ring atoms,

wherein R₉₀₁ to R₉₀₇ each independently represent

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms

a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ringatoms.

In the case where two or more groups each represented by R₉₀₁ exist, thetwo or more groups each represented by R₉₀₁ are the same as or differentfrom each other,

in the case where two or more groups each represented by R₉₀₂ exist, thetwo or more groups each represented by R₉₀₂ are the same as or differentfrom each other,

in the case where two or more groups each represented by R₉₀₃ exist, thetwo or more groups each represented by R₉₀₃ are the same as or differentfrom each other,

in the case where two or more groups each represented by R₉₀₄ exist, thetwo or more groups each represented by R₉₀₄ are the same as or differentfrom each other,

in the case where two or more groups each represented by R₉₀₅ exist, thetwo or more groups each represented by R₉₀₅ are the same as or differentfrom each other,

in the case where two or more groups each represented by R₉₀₆ exist, thetwo or more groups each represented by R₉₀₆ are the same as or differentfrom each other, and

in the case where two or more groups each represented by R₉₀₇ exist, thetwo or more groups each represented by R₉₀₇ are the same as or differentfrom each other.

In one embodiment, the substituent for the case of “substituted orunsubstituted” may be a group selected from the group consisting of

an alkyl group having 1 to 50 carbon atoms,

an aryl group having 6 to 50 ring carbon atoms, and

a heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the substituent for the case of “substituted orunsubstituted” may be a group selected from the group consisting of

an alkyl group having 1 to 18 carbon atoms,

an aryl group having 6 to 18 ring carbon atoms, and

a heterocyclic group having 5 to 18 ring atoms.

The specific examples of the groups for the arbitrary substituentdescribed above are the specific examples of the substituent describedin the section “Substituents in Description” described above.

In the description herein, the arbitrary adjacent substituents may forma “saturated ring” or an “unsaturated ring”, preferably form asubstituted or unsubstituted saturated 5-membered ring, a substituted orunsubstituted saturated 6-membered ring, a substituted or unsubstitutedunsaturated 5-membered ring, or a substituted or unsubstitutedunsaturated 6-membered ring, and more preferably form a benzene ring,unless otherwise indicated.

In the description herein, the arbitrary substituent may further have asubstituent unless otherwise indicated in the description. Thedefinition of the substituent that the arbitrary substituent further hasmay be the same as the arbitrary substituent.

In the description herein, a numerical range shown by “AA to BB” means arange including the numerical value AA as the former of “AA to BB” asthe lower limit value and the numerical value BB as the latter of “AA toBB” as the upper limit value.

The compound of the present invention will be described below.

The compound of the present invention is represented by the followingformula (1). Hereinafter, the compound of the present inventionrepresented by the formula (1) or each formula mentioned later issometimes simply referred to as “the inventive compound”.

Signs in the formula (1) and each formula mentioned later will bedescribed below. The same signs have the same meanings in the followingformulae unless otherwise specified.

In the formula (1),

R¹ to R⁹ are each independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, ahalogen atom, a cyano group, a nitro group, or a substituted orunsubstituted heterocyclic group having 5 to 50 ring atoms.

R¹ to R⁹ are preferably each independently a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 50 carbon atoms, asubstituted or unsubstituted cycloalkyl group having 3 to 50 ring carbonatoms, more preferably each independently a hydrogen atom, a substitutedor unsubstituted alkyl group having 1 to 50 carbon atoms, or asubstituted or unsubstituted cycloalkyl group having 3 to 50 carbonatoms, and further preferably a hydrogen atom.

Details of the halogen atom are as described above in the section“Substituents in Description”, and preferred is a fluorine atom.

Details of the substituted or unsubstituted alkyl group having 1 to 50carbon atoms are as described above in the section “Substituents inDescription”.

The unsubstituted alkyl group is preferably a methyl group, an ethylgroup, an n-propyl group, an isopropyl group, or a t-butyl group, andmore preferably a methyl group, an isopropyl group, or a t-butyl group,

Details of the substituted or unsubstituted cycloalkyl group having 3 to50 ring carbon atoms are as described above in the section “Substituentsin Description”.

The unsubstituted cycloalkyl group is preferably a cyclopropyl group, acyclobutyl group, a cyclopentyl group, a cyclohexyl group, or anadamantyl group.

In an embodiment of the present invention, all of R¹ to R⁹ arepreferably a hydrogen atom.

Adjacent two selected from R¹ to R⁹ are not bonded to each other, thusforming no ring structure.

L¹ is a substituted or unsubstituted arylene group having 6 to 30 ringcarbon atoms or a substituted or unsubstituted divalent heterocyclicgroup having 5 to 30 ring atoms. L¹ is preferably a substituted orunsubstituted arylene group having 6 to 30 ring carbon atoms.

Details of the substituted or unsubstituted arylene group having 6 to 30ring carbon atoms are as described above in the section “Substituents inDescription”.

The unsubstituted arylene group having 6 to 30 ring carbon atoms ispreferably a phenylene group, a biphenylene group, a terphenylene group,or a naphthylene group.

Details of the substituted or unsubstituted divalent heterocyclic grouphaving 5 to 30 ring atoms are as described above in the section“Substituents in Description”.

In an embodiment of the present invention, L¹ is preferably asubstituted or unsubstituted phenylene group, a substituted orunsubstituted biphenylene group, or a substituted or unsubstitutednaphthylene group, and more preferably a substituted or unsubstitutedphenylene group.

L² and L³ are each independently a single bond, a substituted orunsubstituted divalent heterocyclic group having 5 to 30 ring atoms, ora group represented by any of the following formulae (i) to (iii).

In the formulae (i) to (iii),

*a is bonded to one selected from the carbon atoms *1 to *3,

*b is bonded to one selected from the carbon atoms *4 to *6,

*c is bonded to one selected from the carbon atoms *7 to *9,

*d is bonded to one selected from the carbon atoms *10 to *17, *e isbonded to another one selected from the carbon atoms *10 to *17,

* represents a bonding site to the central nitrogen atom, and

** represents a bonding site to Ar¹ or Ar².

In an embodiment of the present invention, L² and L³ are preferably eachindependently a single bond or a group represented by the formula (i) or(ii).

Details of the substituted or unsubstituted divalent heterocyclic grouphaving 5 to 30 ring atoms represented by L² and L³ are as describedabove in the section “Substituents in Description”.

In an embodiment of the present invention, *a is preferably bonded tothe carbon atom *3.

In another embodiment of the present invention, *b is preferably bondedto the carbon atom *6.

In still another embodiment of the present invention, *c is preferablybonded to the carbon atom *7.

Ar¹ and Ar² are each independently a group represented by any of thefollowing formulae (a) to (e).

In the formula (a),

R¹⁰ to R²⁵ are each independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, ahalogen atom, a cyano group, a nitro group, a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms constitutedonly of 6-membered rings, or a substituted or unsubstituted heterocyclicgroup having 5 to 50 ring atoms.

Provided that

one selected from R¹⁰ to R¹⁴ is a single bond bonded to *f,

one selected from R¹⁵ to R²⁰ is a single bond bonded to *g, another oneselected from R¹⁵ to R²⁰ is a single bond bonded to *h,

*** represents a bonding site to L² or L³,

m1 is 0 or 1, n1 is 0 or 1,

when m1 is 0 and n1 is 0, *h is bonded to L² or L³,

when m1 is 0 and n1 is 1, *f is bonded to L² or L³,

when m1 is 1 and n1 is 0, one selected from R¹⁰ to R¹⁴ is a single bondbonded to *h, and

k1 is 1 or 2.

Adjacent two selected from R¹⁰ to R¹⁴ that are not the single bond are,and adjacent two selected from R¹⁵ to R²⁰ that are not either of thesingle bonds are, not bonded to each other, thus forming no ringstructure.

When Ar¹ is a group represented by the formula (a) in which m1 is 0, n1is 0, and L² is a single bond, *h is bonded to the central nitrogenatom.

When Ar² is a group represented by the formula (a) in which m1 is 0, n1is 0, and L³ is a single bond, *h is bonded to the central nitrogenatom.

When Ar¹ is a group represented by the formula (a) in which m1 is 0, n1is 1, and L² is a single bond, *f is bonded to the central nitrogenatom.

When Ar² is a group represented by the formula (a) in which m1 is 0, n1is 1, and L³ is a single bond, *f is bonded to the central nitrogenatom.

When Ar² is a group represented by the formula (a) in which m1 is 1, n1is 1, and L² is a single bond, *** represents a bonding site to thecentral nitrogen atom.

When Ar² is a group represented by the formula (a) in which m1 is 1, n1is 1, and L³ is a single bond, *** represents a bonding site to thecentral nitrogen atom.

k1 is preferably 1.

In an embodiment of the present invention, it is preferred that m1 is 0,n1 is 0, and k1 is 1, in another embodiment, it is preferred that m1 is0, n1 is 1, and k1 is 1, or that m1 is 1, n1 is 0, and k1 is 1. In stillanother embodiment, it is preferred that m1 is 1, n1 is 1, and k1 is 1.In still yet another embodiment, it is preferred that m1 is 1, n1 is 1,and k1 is 2.

In an embodiment of the present invention, at least one of Ar¹ and Ar²is preferably a group represented by the formula (a).

In the formula (b),

R¹⁰ to R²⁰, *f, *g, *h, and *** are the same as described above,

R²⁶ to R³³ are each independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, ahalogen atom, a cyano group, a nitro group, a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms constitutedonly of 6-membered rings, or a substituted or unsubstituted heterocyclicgroup having 5 to 50 ring atoms.

Provided that, one selected from R²⁶ to R*³ is a single bond bonded to*i.

m2 is 0 or 1, n2 is 0 or 1,

when m2 is 0 and n2 is 0, *h is bonded to L² or L³,

when m2 is 0 and n2 is 1, *f is bonded to L² or L³, and

when m2 is 1 and n2 is 0, one selected from R¹⁰ to R¹⁴ is a single bondbonded to *h.

Adjacent two selected from R¹⁰ to R¹⁴ that are not the single bond are,and adjacent two selected from R¹⁵ to R²⁰ that are not either of thesingle bonds are, not bonded to each other, thus forming no ringstructure.

When Ar¹ is a group represented by the formula (b) in which m2 is 0, n2is 0, and L² is a single bond, *h is bonded to the central nitrogenatom.

When Ar² is a group represented by the formula (b) in which m2 is 0, n2is 0, and L³ is a single bond, *h is bonded to the central nitrogenatom.

When Ar¹ is a group represented by the formula (b) in which m2 is 0, n2is 1, and L² is a single bond, *f is bonded to the central nitrogenatom.

When Ar² is a group represented by the formula (b) in which m2 is 0, n2is 1, and L³ is a single bond, *f is bonded to the central nitrogenatom.

When Ar¹ is a group represented by the formula (b) in which m2 is 1, n2is 1, and L² is a single bond, *** represents a bonding site to thecentral nitrogen atom.

When Ar² is a group represented by the formula (b) in which m2 is 1, n2is 1, and L³ is a single bond, *** represents a bonding site to thecentral nitrogen atom.

In an embodiment of the present invention, it is preferred that m2 is 0and n2 is 0, in another embodiment, it is preferred that m2 is 0 and n2is 1, or that m2 is 1 and n2 is 0. In still another embodiment, it ispreferred that m2 is 1 and n2 is 1.

In the formula (c),

R¹⁰ to R²⁰, *f, *g, *h, and *** are the same as described above,

R³⁴ to R⁴³ are each independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, ahalogen atom, a cyano group, a nitro group, a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms constitutedonly of 6-membered rings, or a substituted or unsubstituted heterocyclicgroup having 5 to 50 ring atoms.

Provided that, one selected from R³⁴ to R⁴³ is a single bond bonded to*j.

m3 is 0 or 1, n3 is 0 or 1,

when m3 is 0 and n3 is 0, *h is bonded to L² or L³,

when m3 is 0 and n3 is 1, *f is bonded to L² or L³, and

when m3 is 1 and n2 is 0, one selected from R¹⁰ to R¹⁴ is a single bondbonded to *h.

Adjacent two selected from R¹⁰ to R¹⁴ that are not the single bond are,adjacent two selected from R¹⁵ to R²⁰ that are not either of the singlebonds are, and R³⁴ and R³⁵ are, not bonded to each other, thus formingno ring structure.

In an embodiment of the present invention, R³⁴ or R³⁷ is preferably asingle bond bonded to *j.

When Ar¹ is a group represented by the formula (c) in which m3 is 0, n3is 0, and L² is a single bond, *h is bonded to the central nitrogenatom.

When Ar² is a group represented by the formula (c) in which m3 is 0, n3is 0, and L³ is a single bond, *h is bonded to the central nitrogenatom.

When Ar¹ is a group represented by the formula (c) in which m3 is 0, n3is 1, and L² is a single bond, *f is bonded to the central nitrogenatom.

When Ar² is a group represented by the formula (c) in which m3 is 0, n3is 1, and L³ is a single bond, *f is bonded to the central nitrogenatom.

When Ar¹ is a group represented by the formula (c) in which m3 is 1, n3is 1, and L² is a single bond, *** represents a bonding site to thecentral nitrogen atom.

When Ar² is a group represented by the formula (c) in which m3 is 1, n3is 1, and L³ is a single bond, *** represents a bonding site to thecentral nitrogen atom.

In an embodiment of the present invention, it is preferred that m3 is 0and n3 is 0, and in another embodiment, it is preferred that m3 is 0 andn3 is 1, or that m3 is 1 and n3 is 0. In still another embodiment, it ispreferred that m3 is 1 and n3 is 1.

In the formula (d),

R¹⁰ to R¹⁴, *f, and *** are the same as described above,

R⁴⁴ to R⁵¹ are each independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, ahalogen atom, a cyano group, a nitro group, a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms constitutedonly of 6-membered rings, or a substituted or unsubstituted heterocyclicgroup having 5 to 50 ring atoms.

X is an oxygen atom, a sulfur atom, CR^(a)R^(b), or NR^(c),

R^(a), R^(b), and R^(c) are each independently a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 50 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, or a substituted or unsubstituted heterocyclic group having 5 to50 ring atoms.

Provided that, one selected from R⁴⁴ to R⁵¹ and R^(c) is a single bondbonded to *k.

m4 is 0 or 1, and

when m4 is 0, *f is bonded to L² or LU.

combinations of adjacent two selected from R⁴⁴ to R⁵¹ that are not thesingle bond may each independently be bonded to each other to form asubstituted or unsubstituted ring structure.

R^(a) and R^(b) are not crosslinked.

In an embodiment of the present invention, X is preferably an oxygenatom, CR^(a)R^(b), or NR_(c), and more preferably an oxygen atom.

Details of the substituted or unsubstituted alkyl group having 1 to 50carbon atoms represented by R^(a), R^(b), and Re are as described abovefor R¹ to R⁹.

Details of the substituted or unsubstituted aryl group having 6 to 50ring carbon atoms represented by R^(a), R^(b), and R^(c) are asdescribed above in the section “Substituents in Description”.

The unsubstituted aryl groups having 5 to 50 ring carbon atomsrepresented by R^(a), R^(b), and R^(c) are preferably each independentlyselected from a phenyl group, a biphenyl group, and a naphthyl group.

Details of the substituted or unsubstituted heterocyclic group having 5to 50 carbon atoms represented by R^(a), R^(b), and R^(c) are asdescribed above for R¹ to R⁹.

When Ar¹ is a group represented by the formula (d) in which m4 is 0 andL² is a single bond, *f is bonded to the central nitrogen atom.

When Ar² is a group represented by the formula (d) in which m4 is 0 andL³ is a single bond, *f is bonded to the central nitrogen atom.

When Ar¹ is a group represented by the formula (d) in which m4 is 1 andL² is a single bond, *** represents a bonding site to the centralnitrogen atom.

When Ar² is a group represented by the formula (d) in which m4 is 1 andL³ is a single bond, *** represents a bonding site to the centralnitrogen atom.

In an embodiment of the present invention, m4 is preferably 0, and inanother embodiment, m4 is preferably 1.

In an embodiment of the present invention, combinations of adjacent twoselected from R⁴⁴ to R⁶¹ that are not the single bond are eachindependently not bonded to each other to form a substituted orunsubstituted ring structure.

In the formula (e),

R¹⁰ to R¹⁴, *f, and *** are the same as described above,

R⁵² to R⁶⁶ are each independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, ahalogen atom, a cyano group, a nitro group, a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms constitutedonly of 6-membered rings, or a substituted or unsubstituted heterocyclicgroup having 5 to 50 ring atoms.

Provided that,

one selected from R⁵² to R⁵⁶ is a single bond bonded to *l, another oneselected from R⁵² to R⁵⁶ is a single bond bonded to *m,

m5 is 0 or 1, and

when m5 is 0, *f is bonded to L² or L³.

Adjacent two selected from R¹⁰ to R¹⁴ that are not the single bond are,adjacent two selected from R⁵² to R⁵⁶ that are not either of the singlebonds are, R⁵² and R⁶¹ are, and R⁵⁶ and R⁵⁷ are, not bonded to eachother, thus forming no ring structure.

In an embodiment of the present invention, it is preferred that R⁵³ is asingle bond bonded to *l and R⁵⁶ is a single bond bonded to *m.

When Ar¹ is a group represented by the formula (e) in which m5 is 0 andL² is a single bond, *f is bonded to the central nitrogen atom.

When Ar² is a group represented by the formula (e) in which m5 is 0 andL³ is a single bond, *f is bonded to the central nitrogen atom.

When Ar¹ is a group represented by the formula (e) in which m5 is 1 andL² is a single bond, *** represents a bonding site to the centralnitrogen atom.

When Ar² is a group represented by the formula (e) in which m5 is 1 andL³ is a single bond, *** represents a bonding site to the centralnitrogen atom.

In an embodiment of the present invention, m5 is preferably 0, and inanother embodiment, m5 is preferably 1.

Details of the substituted or unsubstituted aryl group having 6 to 50ring carbon atoms represented by R¹⁰ to R⁶⁶ are as described above inthe section “Substituents in Description”.

The unsubstituted aryl group having 5 to 50 ring carbon atomsrepresented by R¹⁰ to R⁶⁶ are preferably each independently selectedfrom a phenyl group, a biphenyl group, and a naphthyl group.

Details of each group other than the aryl group represented by R¹⁰ toR⁶⁶ are the same as the details of the corresponding group described forR¹ to R⁹.

Ar¹ and Ar² are preferably each independently a group represented by anyof the following formulae (a-1) to (e-1).

In the formulae (a-1) to (e-1),

R¹⁰, R¹¹, R¹³, R¹⁴, R¹⁵ to R¹⁹, R²¹ to R⁶⁶, X, *i, *j, *k, *l, *m, m1,n1, k1, m2, n2, m3, n3, m4, and m5 are as defined in the formula (1).

In an embodiment of the present invention,

in the formula (a), all of R¹⁰ to R¹⁴ that are not the single bondbonded to *f may be a hydrogen atom,

in the formula (a), all of R¹⁵ to R²⁰ that are not the single bondbonded to *g nor the single bond bonded to *h may be a hydrogen atom,and

all of R²¹ to R²⁵ may be a hydrogen atom,

in the formula (b), all of R¹⁰ to R¹⁴ that are not the single bondbonded to *f may be a hydrogen atom,

in the formula (b), all of R¹⁵ to R²⁰ that are not the single bondbonded to *g nor the single bond bonded to *h may be a hydrogen atom,and

all of R²⁶ to R³³ that are not the single bond bonded to *i may be ahydrogen atom,

in the formula (c), all of R¹⁰ to R¹⁴ that are not the single bondbonded to *f may be a hydrogen atom,

in the formula (c), all of R¹⁵ to R²⁰ that are not the single bondbonded to *g nor the single bond bonded to *h may be a hydrogen atom,and

all of R³⁴ to R⁴³ that are not the single bond bonded to *j may be ahydrogen atom,

in the formula (d), all of R¹⁰ to R¹⁴ that are not the single bondbonded to *f may be a hydrogen atom, and

all of R⁴⁴ to R⁵¹ that are not the single bond bonded to *k may be ahydrogen atom, and

in the formula (e), all of R¹⁰ to R¹⁴ that are not the single bondbonded to *f may be a hydrogen atom,

all of R⁵² to R⁵⁶ that are not the single bond bonded to *l nor thesingle bond bonded to *m may be a hydrogen atom,

all of R⁵⁷ to R⁶¹ may be a hydrogen atom, and

all of R⁵² to R⁶⁶ may be a hydrogen atom.

As described above, a “hydrogen atom” as used herein includes a lighthydrogen atom, a deuterium atom, and a tritium atom. Thus, the inventivecompound may contain a naturally-derived deuterium atom.

A deuterium atom may also be intentionally introduced in the inventivecompound by using a deuterated compound in a part or all of raw materialcompounds. Thus, in an embodiment of the present invention, theinventive compound contains at least one deuterium atom. Specifically,the inventive compound may be a compound represented by formula (1), atleast one of the hydrogen atoms contained in the compound being adeuterium atom.

At least one hydrogen atom selected from the following hydrogen atomsmay be a deuterium atom:

a hydrogen atom represented by any of R¹ to R⁹; a hydrogen atom of asubstituted or unsubstituted alkyl group, a cycloalkyl group, a halogenatom, a cyano group, a nitro group, or a heterocyclic group representedby any of R¹ to R⁹;

a hydrogen atom represented by any of R¹⁰ to R²⁵; a hydrogen atom of asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedcycloalkyl group, a halogen atom, a cyano group, a nitro group, asubstituted or unsubstituted aryl group constituted only of 6-memberedrings, or a substituted or unsubstituted heterocyclic group representedby any of R¹⁰ to R²⁵;

a hydrogen atom represented by any of R²⁶ to R³³; a hydrogen atom of asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedcycloalkyl group, a halogen atom, a cyano group, a nitro group, asubstituted or unsubstituted aryl group constituted only of 6-memberedrings, or a substituted or unsubstituted a heterocyclic grouprepresented by any of R²⁶ to R³³;

a hydrogen atom represented by any of R³⁴ to R⁴³; a hydrogen atom of asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedcycloalkyl group, a halogen atom, a cyano group, a nitro group, asubstituted or unsubstituted aryl group constituted only of 6-memberedrings, or a substituted or unsubstituted heterocyclic group representedby any of R³⁴ to R⁴³;

a hydrogen atom represented by any of R⁴⁴ to R⁵¹; a hydrogen atom of asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedcycloalkyl group, a halogen atom, a cyano group, a nitro group, asubstituted or unsubstituted aryl group constituted only of 6-memberedrings, or a substituted or unsubstituted heterocyclic group representedby any of R⁴⁴ to R⁵¹;

a hydrogen atom represented by any of R^(a), R^(b), and R^(c); ahydrogen atom of a substituted or unsubstituted alkyl group, asubstituted or unsubstituted aryl group, or a substituted orunsubstituted heterocyclic group represented by any of R^(a), R^(b), andR^(c);

a hydrogen atom of a substituted or unsubstituted arylene group or asubstituted or unsubstituted divalent heterocyclic group represented byL¹; and

a hydrogen atom of a substituted or unsubstituted divalent heterocyclicgroup represented by either of L² and L³; a hydrogen atom of a grouprepresented by the any of the formulae (i) to (iii) represented byeither of L² and LU.

The deuteration ratio of the inventive compound depends on thedeuteration ratio of the raw material compound used. Even when a rawmaterial having a predetermined deuteration ratio is used, lighthydrogen isomers may be contained at a certain naturally-derived ratio.Thus, the embodiments of the deuteration ratio of the inventive compoundshown below are a ratio obtained by taking a minor amount ofnaturally-derived isomers into account based on a ratio obtained bysimply counting the number of deuterium atoms shown by the chemicalformula.

The deuteration ratio of the inventive compound is preferably 1% ormore, more preferably 3% or more, further preferably 5% or more,furthermore preferably 10% or more, and still furthermore preferably 50%or more.

The inventive compound may be a mixture containing a deuterated compoundand a non-deuterated compound or a mixture of two or more compoundshaving different deuteration ratios. The deuteration ratio of such amixture is preferably 1% or more, more preferably 3% or more, furtherpreferably 5% or more, further preferably 10% or more, furthermorepreferably 50% or more, and less than 100%.

The ratio of the number of the deuterium atoms based on the number ofall the hydrogen atoms in the inventive compound is preferably 1% ormore, more preferably 3% or more, further preferably 5% or more, furtherpreferably 10% or more, and 100% or less.

Details of the substituent (arbitrary substituent) in the “substitutedor unsubstituted” included in the definition of each formula asmentioned above are as described in the section “Substituent for“Substituted or Unsubstituted””.

Here, said arbitrary substituent in the definition of each formulaaccording to the formula (1) does not include an aryl group, aheterocyclic group, and the substituent in which R₉₀₁ to R₉₀₇ are aheterocyclic group among the substituents described in the section“Substituent for “Substituted or Unsubstituted””.

The inventive compound can be easily produced by a person skilled in theart with reference to synthetic examples described below and knownsynthetic methods.

Specific examples of the inventive compound will be shown below, butwere not limited to the exemplified compounds.

In the following specific examples, D represents a deuterium atom.

[Material for Organic EL Devices]

The material for organic EL devices as an aspect of the presentinvention contains the inventive compound. The content of the inventivecompound in the material for organic EL devices is 1% by mass or more(including 100%), preferably 10% by mass or more (including 100%), morepreferably 50% by mass or more (including 100%), further preferably 80%by mass or more (including 100%), and particularly preferably 90% bymass or more (including 100%). The material for organic EL devices as anaspect of the present invention is useful for production of an organicEL device.

Organic EL Device

The organic EL device as an aspect of the present invention includes ananode, a cathode, and organic layers disposed between the anode and thecathode. The organic layers include a light emitting layer and at leastone of the organic layers contains the inventive compound.

Examples of the organic layer containing the inventive compound include,but not limited to, a hole transporting zone (hole injecting layer, holetransporting layer, electron blocking layer, exciton blocking layer,etc.) provided between the anode and the light emitting layer, the lightemitting layer, a space layer, an electron transporting zone (electroninjecting layer, electron transporting layer, hole blocking layer, etc.)provided between the cathode and the light emitting layer. The inventivecompound is preferably used as a material for the hole transporting zoneor light emitting layer, more preferably as a material for the holetransporting zone, further preferably as a material for the holeinjecting layer, hole transporting layer, electron blocking layer, orexciton blocking layer, and particularly preferably as a material forthe hole injecting layer or hole transporting layer, of a fluorescent orphosphorescent EL device.

The organic EL device as an aspect of the present invention may be afluorescence or phosphorescence emission type monochromatic luminescentdevice, a fluorescence/phosphorescence hybrid type white luminescentdevice, a simple type having a single light emitting unit, or a tandemtype having two or more light emitting units, and is preferably afluorescence emission type device. Here, the “light emitting unit”refers to a minimum unit that includes organic layers, at least one ofwhich is a light emitting layer, and that emits light by recombinationof injected holes and injected electrons.

An example of a typical device configuration of the simple type organicEL device is the following device configuration.

(1) Anode/Light Emitting Unit/Cathode

The light emitting unit may be a multilayer type having two or morephosphorescence emitting layers and fluorescence emitting layers, and inthis case, a space layer may be provided between the light emittinglayers for the purpose of preventing excitons generated in thephosphorescence emitting layers from diffusing into the fluorescenceemitting layers. A typical layer configuration of the simple type lightemitting unit is shown below. The layers in parentheses are optional.

(a) (hole injecting layer/) hole transporting layer/fluorescenceemitting layer/electron transporting layer (/electron injecting layer)

(b) (hole injecting layer/) hole transporting layer/phosphorescenceemitting layer electron transporting layer (/electron injecting layer)

(c) (hole injecting layer/) hole transporting layer/first fluorescenceemitting layer/second fluorescence emitting layer/electron transportinglayer (/electron injecting layer)

(d) (hole injecting layer/) hole transporting layer/firstphosphorescence emitting layer/second phosphorescence emittinglayer/electron transporting layer (/electron injecting layer)

(e) (hole injecting layer/) hole transporting layer/phosphorescenceemitting layer/space layer/fluorescence emitting layer/electrontransporting layer (/electron injecting layer)

(f) (hole injecting layer/) hole transporting layer/firstphosphorescence emitting layer/second phosphorescence emittinglayer/space layer/fluorescence emitting layer/electron transportinglayer (/electron injecting layer)

(g) (hole injecting layer/) hole transporting layer/firstphosphorescence emitting layer/space layer/second phosphorescenceemitting layer/space layer/fluorescence emitting layer/electrontransporting layer (/electron injecting layer)

(h) (hole injecting layer/) hole transporting layer/phosphorescenceemitting layer/space layer/first fluorescence emitting layer/secondfluorescence emitting layer/electron transporting layer (/electroninjecting layer)

(i) (hole injecting layer/) hole transporting layer/electron blockinglayer/fluorescence emitting layer/electron transporting layer (/electroninjecting layer)

(j) (hole injecting layer/) hole transporting layer/electron blockinglayer/phosphorescence emitting layer/electron transporting layer(/electron injecting layer)

(k) (hole injecting layer/) hole transporting layer/exciton blockinglayer/fluorescence emitting layer/electron transporting layer (/electroninjecting layer)

(l) (hole injecting layer/) hole transporting layer/exciton blockinglayer/phosphorescence emitting layer/electron transporting layer(/electron injecting layer)

(m) (hole injecting layer/) first hole transporting layer/second holetransporting layer/fluorescence emitting layer/electron transportinglayer (/electron injecting layer)

(n) (hole injecting layer/) first hole transporting layer/second holetransporting layer/phosphorescence emitting layer/electron transportinglayer (/electron injecting layer)

(o) (hole injecting layer/) first hole transporting layer/second holetransporting layer/fluorescence emitting layer/first electrontransporting layer/second electron transporting layer (/electroninjecting layer)

(p) (hole injecting layer/) first hole transporting layer/second holetransporting layer/phosphorescence emitting layer/first electrontransporting layer/second electron transporting layer (/electroninjecting layer)

(q) (hole injecting layer/) hole transporting layer/fluorescenceemitting layer/hole blocking layer/electron transporting layer(/electron injecting layer)

(r) (hole injecting layer/) hole transporting layer/phosphorescenceemitting layer/hole blocking layer/electron transporting layer(/electron injecting layer)

(s) (hole injecting layer/) hole transporting layer/fluorescenceemitting layer/exciton blocking layer/electron transporting layer(/electron injecting layer)

(t) (hole injecting layer/) hole transporting layer/phosphorescenceemitting layer/exciton blocking layer/electron transporting layer(/electron injecting layer)

The phosphorescence or fluorescence emitting layers described above canexhibit luminescent colors different from one another. A specificexample of the layer configuration is a layer configuration in the lightemitting unit (f) of (hole injecting layer/) hole transportinglayer/first phosphorescence emitting layer (red light emission)/secondphosphorescence emitting layer (green light emission)/spacelayer/fluorescence emitting layer (blue light emission)/electrontransporting layer.

An electron blocking layer may be appropriately provided between eachlight emitting layer and a hole transporting layer or a space layer. Inaddition, a hole blocking layer may be appropriately provided betweeneach light emitting layer and an electron transporting layer. Byproviding an electron blocking layer or hole blocking layer, electronsor holes can be trapped inside the light emitting layer to increase theprobability of recombination of charges in the light emitting layer,thus enhancing the light emitting efficiency.

An example of a typical device configuration of the tandem type organicEL device is the following device configuration.

(2) Anode/First Light Emitting Unit/Intermediate Layer/Second LightEmitting Unit/Cathode

Here, the first light emitting unit and the second light emitting unitcan each be independently selected, for example, from the light emittingunits as described above.

The intermediate layer is generally also referred to as intermediateelectrode, intermediate conductive layer, charge generating layer,electron withdrawing layer, connection layer, or intermediate insulatinglayer, and a known material configuration in which electrons aresupplied to the first light emitting unit and holes are supplied to thesecond light emitting unit can be used.

FIG. 1 is a schematic diagram illustrating an example of theconfiguration of the organic EL device according to an aspect of thepresent invention. An organic EL device 1 includes a substrate 2, ananode 3, a cathode 4, and a light emitting unit 10 disposed between theanode 3 and the cathode 4. The light emitting unit 10 includes a lightemitting layer 5. The organic EL device 1 includes a hole transportingzone 6 (hole injecting layer, hole transporting layer, etc.) between thelight emitting layer 5 and the anode 3, and an electron transportingzone 7 (electron injecting layer, electron transporting layer, etc.)between the light emitting layer 5 and the cathode 4. In addition, anelectron blocking layer (not shown) may be provided on the anode 3 sideof the light emitting layer 5 and a hole blocking layer (not shown) maybe provided on the cathode 4 side of the light emitting layer 5. Thisenables to trap electrons or holes in the light emitting layer 5 tofurther increase the efficiency of generating excitons in the lightemitting layer 5.

FIG. 2 is a schematic diagram illustrating another configuration of theorganic EL device according to an aspect of the present invention. Anorganic EL device 11 includes the substrate 2, the anode 3, the cathode4, and a light emitting unit 20 disposed between the anode 3 and thecathode 4. The light emitting unit 20 includes the light emitting layer5. A hole transporting zone disposed between the anode 3 and the lightemitting layer 5 is formed of a hole injecting layer 6 a, a first holetransporting layer 6 b, and a second hole transporting layer 6 c. Theelectron transporting zone disposed between the light emitting layer 5and the cathode 4 is formed of a first electron transporting layer 7 aand a second electron transporting layer 7 b.

In the present invention, a host combined with a fluorescent dopant(fluorescence emitting material) is referred to as a fluorescent host,and a host combined with a phosphorescent dopant is referred to as aphosphorescent host. The fluorescent host and the phosphorescent hostare not distinguished only by the molecular structure. In other words,the phosphorescent host means a material that forms a phosphorescenceemitting layer containing a phosphorescent dopant, and does not meanthat it cannot be used as a material that forms a fluorescence emittinglayer. The same applies to the fluorescent host.

Substrate

The substrate is used as a support of the organic EL device. As thesubstrate, for example, a plate of glass, quartz, or a plastic can beused. A flexible substrate may be used. An example of the flexiblesubstrate is a plastic substrate of polycarbonate, polyarylate,polyethersulfone, polypropylene, polyester, polyvinyl fluoride, orpolyvinyl chloride. An inorganic vapor deposition film can also be used.

Anode

For the anode formed on the substrate, a metal, an alloy, anelectrically conductive compound, a mixture thereof, or the like thathas a high work function (specifically 4.0 eV or more) is preferablyused. Specific examples thereof include indium oxide-tin oxide (ITO:indium tin oxide), indium oxide-tin oxide containing silicon or siliconoxide, indium oxide-zinc oxide, indium oxide containing tungsten oxideand zinc oxide, and graphene. Other examples include gold (Au), platinum(Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron(Fe), cobalt (Co), cupper (Cu), palladium (Pd), titanium (Ti), andnitride of the metals (for example, titanium nitride).

A film of such a material is generally formed by a spattering method.For example, indium oxide-zinc oxide can be formed by a spatteringmethod by using a target obtained by adding to indium oxide 1 to 10 wt %of zinc oxide based on the indium oxide, and indium oxide containingtungsten oxide and zinc oxide can be formed by a spattering method byusing a target obtained by adding to indium oxide 0.5 to 5 wt % oftungsten oxide and 0.1 to 1 wt % of zinc oxide based on the indiumoxide. Alternatively, a film of such a material may be produced by avacuum vapor deposition method, a coating method, an inkjet method, aspin-coating method, or the like.

The hole injecting layer formed in contact with the anode is, regardlessof the work function of the anode, formed by using a material in whichhole injection is easy, and thus a material that is generally used as anelectrode material (for example, a metal, an alloy, an electricallyconductive compound, or a mixture thereof, or an element belonging tothe group 1 or 2 in the periodic table) can be used.

An element belonging to the group 1 or 2 in the periodic table which isa material having a small work function, specifically, an alkali metal,such as lithium (Li) or cesium (Cs), or an alkaline earth metal, such asmagnesium (Mg), calcium (Ca), or strontium (Sr), and an alloy containingthem (for example, MgAg, AlLi), a rare earth metal, such as europium(Eu) or ytterbium (Yb), or an alloy containing them, or the like, can beused. When the anode is formed using an alkali metal, an alkaline earthmetal, or an alloy containing them, a vacuum vapor deposition method ora spattering method can be adopted. When silver paste or the like isused, a coating method, an inkjet method, or the like can be adopted.

Hole Injecting Layer

The hole injecting layer is a layer containing a material having a highhole injecting capability (hole injecting material), and is formedbetween the anode and the light emitting layer, or between a holetransporting layer, if present, and the anode.

As a hole injecting material other than the inventive compound,molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide,ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide,tantalum oxide, silver oxide, tungsten oxide, manganese oxide, or thelike can be used.

Other examples of a material for the hole injecting layer includearomatic amine compounds, such as4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA),4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine(abbreviation: MTDATA),4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation:DPAB),4,4′-bis(N-{4-[N′-(3-methylphenyl)-N′-phenylamino]phenyl}-N-phenylamino)biphenyl(abbreviation: DNTPD),1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene(abbreviation: DPA3B),3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole(abbreviation: PCzPCA1),3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole(abbreviation: PCzPCA2), and3-[N-(1-naphtyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole(abbreviation: PCzPCN1), which are low-molecular weight organiccompounds.

A high-molecular weight compound (oligomer, dendrimer, polymer, or thelike) can also be used. Examples of the high-molecular weight compoundinclude poly(N-vinylcarbazole) (abbreviation: PVK),poly(4-vinyltriphenylamine) (abbreviation: PVTPA),poly[N-(4-{N′-[4-(4-diphenylamino)phenyl]phenyl-N′-phenylamino}phenyl)methacrylamide](abbreviation: PTPDMA), andpoly[N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine] (abbreviation:Poly-TPD). A high-molecular weight compound with an acid, such aspoly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS)or polyaniline/poly(styrenesulfonic acid) (PAni/PSS), added thereto canalso be used.

Furthermore, an acceptor material, such as a hexaazatriphenylene (HAT)compound represented by the following formula (K), is also preferablyused.

(In the formula, R²⁰¹ to R²⁰⁶ each independently represent a cyanogroup, —CONH₂, a carboxy group, or —COOR²⁰⁷ (R²⁰⁷ represents an alkylgroup having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20carbon atoms). Adjacent two selected from R²⁰¹ and R²⁰², R²³ and R²⁴,and R²⁵ and R²⁰ may be bonded to each other to form a group representedby —CO—O—CO—.)

Examples of R²⁰⁷ include a methyl group, an ethyl group, an n-propylgroup, an isopropyl group, an n-butyl group, an isobutyl group, at-butyl group, a cyclopentyl group, and a cyclohexyl group.

Hole Transporting Layer

The hole transporting layer is a layer containing a material having ahigh hole transporting capability (hole transporting material), and isformed between the anode and the light emitting layer or between a holeinjecting layer, if present, and the light emitting layer. The inventivecompound may be used, for the hole transporting layer, alone or incombination with the following compound.

The hole transporting layer may have a monolayer structure or amultilayer structure including two or more layers. For example, the holetransporting layer may have a two-layer structure including a first holetransporting layer (anode side) and a second hole transporting layer(cathode side). In an embodiment of the present invention, the holetransporting layer of the monolayer structure is preferably adjacent tothe light emitting layer, and the hole transporting layer that is thenearest to the cathode in the multilayer structure, for example, thesecond hole transporting layer in the two-layer structure, is preferablyadjacent to the light emitting layer. In another embodiment of thepresent invention, an electron blocking layer as described later or thelike may be interposed between the hole transporting layer of themonolayer structure and the light emitting layer or between the holetransporting layer that is the nearest to the light emitting layer inthe multilayer structure and the light emitting layer.

In the hole transporting layer of the two-layer configuration, theinventive compound may be contained in one of the first holetransporting layer and the second hole transporting layer, or may becontained in the both.

In an embodiment of the present invention, the inventive compound ispreferably contained only in the first hole transporting layer, inanother embodiment, the inventive compound is preferably contained onlyin the second hole transporting layer, and in still another embodiment,the inventive compound is preferably contained in the first holetransporting layer and the second hole transporting layer.

In an embodiment of the present invention, the inventive compoundcontained in one or both of the first hole transporting layer and thesecond hole transporting layer is preferably a light hydrogen form fromthe viewpoint of the production cost.

The light hydrogen form refers to the inventive compound in which allthe hydrogen atoms are a light hydrogen atom.

Accordingly, the organic EL device as an aspect of the present inventionis preferably an organic EL device in which one or both of the firsthole transporting layer and the second hole transporting layer containsthe inventive compound essentially constituted only of light hydrogenforms. “The inventive compound essentially constituted only of lighthydrogen forms” means that the content of the light hydrogen form basedon the total amount of the inventive compound is 90% by mole or more,preferably 95% by mole or more, and more preferably 99% by mole or more(each including 100%).

As a material for the hole transporting layer other than the inventivecompound, for example, an aromatic amine compound, a carbazolederivative, an anthracene derivative, or the like can be used.

Examples of the aromatic amine compound include4,4′-bis[N-(1-naphtyl)-N-phenylamino]biphenyl (abbreviation: NPB) andN,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine(abbreviation: TPD), 4-phenyl-4′-(9-phenylfluorene-9-yl)triphenylamine(abbreviation: BAFLP),4,4′-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl(abbreviation: DFLDPBi), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine(abbreviation: TDATA),4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine(abbreviation: MTDATA), and4,4′-bis[N-(spiro-9,9′-bifluoren-2-yl)-N-phenylamino]biphenyl(abbreviation: BSPB). The compounds have a hole mobility of 10⁻⁶ cm²/Vsor more.

Examples of the carbazole derivative include4,4′-di(9-carbazolyl)biphenyl (abbreviation: CBP),9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation:PCzPA).

Examples of the anthracene derivative include2-t-butyl-9,10-di(2-naphtyl)anthracene (abbreviation: t-BuDNA),9,10-di(2-naphtyl)anthracene (abbreviation: DNA), and9,10-diphenylanthracene (abbreviation: DPAnth).

A high-molecular weight compound, such as poly(N-vinylcarbazole)(abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation:PVTPA), can also be used.

However, compounds other than those mentioned above may be used so longas they are materials higher in the hole transporting capability ratherthan in the electron transporting capability.

Dopant Material for Light Emitting Layer

The light emitting layer is a layer containing a material having a highlight emitting capability (dopant material), and various materials canbe used. For example, a fluorescence emitting material or aphosphorescence emitting material can be used as the dopant material. Afluorescence emitting material is a compound that emits light from thesinglet excited state, and a phosphorescence emitting material is acompound that emits light from the triplet excited state.

As a blue fluorescence emitting material that can be used for the lightemitting layer, a pyrene derivative, a styrylamine derivative, achrysene derivative, a fluoranthene derivative, a fluoran derivative, adiamine derivative, or a triarylamine derivative can be used. Specificexamples thereof includeN,N′-bis[4-(9H-carbazol-9-yl)phenyl]-N,N′-diphenylstilbene-4,4′-diamine(abbreviation: YGA2S),4-(9H-carbazol-9-yl)-4′-(10-phenyl-9-anthryl)triphenylamine(abbreviation: YGAPA), and4-(10-phenyl-9-anthryl)-4′-(9-phenyl-9H-carbazol-3-yl)triphenylamine(abbreviation: PCBAPA).

As the green fluorescence emitting material that can be used in thelight emitting layer, an aromatic amine derivative or the like can beused. Specific examples thereof includeN-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine(abbreviation: 2PCAPA),N-[9,10-bis(1,1′-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine(abbreviation: 2PCABPhA),N-(9,10-diphenyl-2-anthryl)-N,N′,N′-triphenyl-1,4-phenylenediamine(abbreviation: 2DPAPA),N-[9,10-bis(1,1′-biphenyl-2-yl)-2-anthryl]-N,N′,N′-triphenyl-1,4-phenylenediamine(abbreviation: 2DPABPhA),N-[9,10-bis(1,1′-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracene-2-amine(abbreviation: 2YGABPhA), and N,N,9-triphenylanthracene-9-amine(abbreviation: DPhAPhA).

As a red fluorescence emitting material that can be used in the lightemitting layer, a tetracene derivative, a diamine derivative, or thelike can be used. Specific examples thereof includeN,N,N′,N′-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation:p-mPhTD) and7,14-diphenyl-N,N,N′,N′-tetrakis(4-methylphenyl)acetonaphtho[1,2-a]fluoranthene-3,10-diamine(abbreviation: p-mPhAFD).

As a blue phosphorescence emitting material that can be used in thelight emitting layer, a metal complex, such as an iridium complex, anosmium complex, or a platinum complex, is used. Specific examplesthereof includebis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III)tetrakis(1-pyrazolyl)borate (abbreviation: FIr6),bis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III) picolinate(abbreviation: FIrpic),bis[2-(3′,5′-bistrifluoromethylphenyl)pyridinato-N,C2′]iridium(III)picolinate (abbreviation: Ir(CF3ppy)2(pic)), andbis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(II) acetylacetonate(abbreviation: FIracac).

As a green phosphorescence emitting material that can be used in thelight emitting layer, an iridium complex or the like is used. Examplesthereof include tris(2-phenylpyridinato-N,C2′)iridium(III)(abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2′)iridium(III)acetylacetonate (abbreviation: Ir(ppy)2(acac)),bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate(abbreviation: Ir(pbi)2(acac)), and bis(benzo[h]quinolato)iridium(III)acetylacetonate (abbreviation: Ir(bzq)2(acac)).

As a red phosphorescence emitting material that can be used in the lightemitting layer, a metal complex, such as an iridium complex, a platinumcomplex, a terbium complex, or a europium complex, is used. Specificexamples thereof include organic metal complexes, such asbis[2-(2′-benzo[4,5-a]thienyl)pyridinato-N,C3′]iridium(III)acetylacetonate (abbreviation: Ir(btp)2(acac)),bis(1-phenylisoquinolinato-N,C2′)iridium(II) acetylacetonate(abbreviation: Ir(piq)2(acac)),(acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III)(abbreviation: Ir(Fdpq)2(acac)), and2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II)(abbreviation: PtOEP).

In addition, a rare earth metal complex, such astris(acetylacetonate)(monophenanthroline)terbium(III) (abbreviation:Tb(acac)3(Phen)),tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III)(abbreviation: Eu(DBM)3(Phen)), ortris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III)(abbreviation: Eu(TTA)3(Phen)), emits light from rare earth metal ions(electron transition between different multiplicities) and thus, can beused as a phosphorescence emitting material.

Host Material for Light Emitting Layer

The light emitting layer may have a configuration in which such a dopantmaterial as described above is dispersed in another material (hostmaterial). A material that has a higher lowest unoccupied molecularorbital level (LUMO level) and a lower highest occupied molecularorbital level (HOMO level) than the dopant material is preferably used.

As the host material, for example,

(1) a metal complex, such as an aluminum complex, a beryllium complex,or a zinc complex,

(2) a heterocyclic compound, such as an oxadiazole derivative, abenzimidazole derivative, or a phenanthroline derivative,

(3) a condensed aromatic compound, such as a carbazole derivative, ananthracene derivative, a phenanthrene derivative, a pyrene derivative,or a chrysene derivative, or

(4) an aromatic amine compound, such as a triarylamine derivative or acondensed polycyclic aromatic amine derivative is used.

For example, a metal complex, such as tris(8-quinolinolato)aluminum(III)(abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III)(abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II)(abbreviation: BeBq2),bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III)(abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq),bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), orbis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ);

a heterocyclic compound, such as2-(4-biphenyly)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation:PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene(abbreviation: OXD-7),3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole(abbreviation: TAZ),2,2′,2″-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole)(abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), orbathocuproine (abbreviation: BCP);

a condensed aromatic compound, such as9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA),3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole(abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene(abbreviation: DPPA), 9,10-di(2-naphtyl)anthracene (abbreviation: DNA),2-tert-butyl-9,10-di(2-naphtyl)anthracene (abbreviation: t-BuDNA),9,9′-bianthryl (abbreviation: BANT),9,9′-(stilbene-3,3′-diyl)diphenanthrene (abbreviation: DPNS),9,9′-(stilbene-4,4′-diyl)diphenanthrene (abbreviation: DPNS2),3,3′,3″-(benzene-1,3,5-triyl)tripyrene (abbreviation: TPB3),9,10-diphenylanthracene (abbreviation: DPAnth), or6,12-dimethoxy-5,11-diphenylchrysene; and

an aromatic amine compound, such asN,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine(abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine(abbreviation: DPhPA),N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine(abbreviation: PCAPA),N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazole-3-amine(abbreviation: PCAPBA),N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine(abbreviation: 2PCAPA), 4,4′-bis[N-(1-naphtyl)-N-phenylamino]biphenyl(abbreviation: NPB or α-NPD),N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine(abbreviation: TPD),4,4′-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl(abbreviation: DFLDPBi), or4,4′-bis[N-(spiro-9,9′-bifluoren-2-yl)-N-phenylamino]biphenyl(abbreviation: BSPB), can be used. Two or more host materials may beused.

In particular, in the case of the blue fluorescence device, thefollowing anthracene compounds are preferably used as a host material.

Electron Transporting Layer

The electron transporting layer is a layer containing a material havinga high electron transporting capability (electron transportingmaterial), and is formed between the light emitting layer and thecathode or between an electron injecting layer, if present, and thelight emitting layer.

The electron transporting layer may have a monolayer structure or amultilayer structure including two or more layers. For example, theelectron transporting layer may have a two-layer structure including afirst electron transporting layer (anode side) and a second electrontransporting layer (cathode side). In an embodiment of the presentinvention, the electron transporting layer in the monolayer structure ispreferably adjacent to the light emitting layer, and the electrontransporting layer that is the nearest to the anode in the multilayerconfiguration, for example, the first electron transporting layer of thetwo-layer structure, is preferably adjacent to the light emitting layer.In another embodiment of the present invention, a hole blocking layer asdescribed later or the like may be interposed between the electrontransporting layer of the monolayer structure and the light emittinglayer or between the electron transporting layer that is the nearest tothe light emitting layer in the multilayer structure and the lightemitting layer.

For the electron transporting layer, for example,

-   -   (1) a metal complex, such as an aluminum complex, a beryllium        complex, or a zinc complex,    -   (2) a heteroaromatic compound, such as an imidazole derivative,        a benzinmidazole derivative, an azine derivative, a carbazole        derivative, or a phenanthroline derivative, or    -   (3) a high-molecular weight compound        can be used.

Examples of the metal complex include tris(8-quinolinolato)aluminum(III)(abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(abbreviation: BeBq₂),bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III)(abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq),bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), andbis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).

Examples of the heteroaromatic compound include2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation:PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene(abbreviation: OXD-7),3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole(abbreviation: TAZ),3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole(abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen),bathocuproine (abbreviation: BCP), and4,4′-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs).

Examples of the high-molecular weight compound includepoly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)](abbreviation: PF-Py) andpoly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)](abbreviation: PF-BPy).

The materials are materials having an electron mobility of 10⁻⁶ cm²Vs ormore. Materials other than those as mentioned above may be used for theelectron transporting layer so long as they are materials higher in theelectron transporting capability rather than in the hole transportingcapability.

Electron Injecting Layer

The electron injecting layer is a layer containing a material having ahigh electron injecting capability. In the electron injecting layer, analkali metal, such as lithium (Li) or cesium (Cs), an alkaline earthmetal, such as magnesium (Mg), calcium (Ca), or strontium (Sr), a rareearth metal, such as europium (Eu) or ytterbium (Yb), and a compoundcontaining them can be used. Examples of the compound include an alkalimetal oxide, an alkali metal halide, an alkali metal-containing organiccomplex, an alkaline earth metal oxide, an alkaline earth metal halide,an alkaline earth metal-containing organic complex, a rare earth metaloxide, a rare earth metal halide, and a rare earth metal-containingorganic complex. In addition, two or more of the compounds can be usedin mixture.

Besides, a material in which an alkali metal, an alkaline earth metal,or a compound thereof is contained in a material having electrontransporting capability, specifically, a material in which magnesium(Mg) is contained in Alq, or the like, may be used. In this case,electron injection from the cathode can be more efficiently achieved.

Alternatively, a composite material obtained by mixing an organiccompound with an electron doner may be used in the injecting layer. Sucha composite material is excellent in the electron injecting capabilityand the electron transporting capability because the organic compoundreceives electrons from the electron doner. In this case, the organiccompound is preferably a material excellent in transporting receivedelectrons, and specifically, a material constituting the aforementionedelectron transporting layer (such as a metal complex or a heteroaromaticcompound) can be used. As the electron donor, a material having anelectron donation capability for an organic compound can be used.Specifically, an alkali metal, an alkaline earth metal, and a rare earthmetal are preferred, and examples thereof include lithium, cesium,magnesium, calcium, erbium, and ytterbium. An alkali metal oxide or analkaline earth metal oxide is also preferred, and examples thereofinclude lithium oxide, calcium oxide, and barium oxide. A Lewis base,such as magnesium oxide, can also be used. An organic compound, such astetrathiafulvalene (abbreviation: TTF), can also be used.

Cathode

A metal, an alloy, an electrically conductive compound, or a mixturethereof that has a low work function (specifically 3.8 eV or less) ispreferably used for the cathode. Specific examples of such a cathodematerial include elements belonging to the group 1 or 2 of the periodictable, that is, an alkali metal, such as lithium (Li) or cesium (Cs), analkaline earth metal, such as magnesium (Mg), calcium (Ca), or strontium(Sr), and an alloy containing them (for example, MgAg, AlLi), and a rareearth metal, such as europium (Eu) or ytterbium (Yb), and an alloycontaining them.

When the cathode is formed by using an alkali metal, an alkaline earthmetal, and an alloy containing them, a vacuum vapor deposition method ora sputtering method can be adopted. When silver paste or the like isused, a coating method, an inkjet method, or the like can be adopted.

By providing the electron injecting layer, the cathode can be formedusing various conductive materials, such as Al, Ag, ITO, graphene, andindium oxide-tin oxide containing silicon or silicon oxide, regardlessof the magnitude of the work function. A film of such a conductivematerial can be formed by using a sputtering method, an inkjet method, aspin-coating method, or the like.

Insulating Layer

The organic EL device applies an electric field to an ultrathin film,and thus, pixel defects are likely to occur due to leaks orshort-circuiting. In order to prevent this, an insulating layer formedof an insulating thin film layer may be inserted between a pair ofelectrodes.

Examples of the material used for the insulating layer include aluminumoxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide,magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride,aluminum nitride, titanium oxide, silicon oxide, germanium oxide,silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, andvanadium oxide. A mixture or a laminate of them may also be used.

Space Layer

The space layer is, for example, a layer provided between a fluorescenceemitting layer and a phosphorescence emitting layer for the purpose ofpreventing excitons generated in the phosphorescence emitting layer fromdiffusing into the fluorescence emitting layer, or adjusting the carrierbalance, in the case where the fluorescence emitting layers and thephosphorescence emitting layers are stacked. The space layer can also beprovided between two or more phosphorescence emitting layers.

Since the space layer is provided between the light emitting layers, amaterial having both an electron transporting capability and a holetransporting capability is preferred. In addition, one having a tripletenergy of 2.6 eV or more is preferred in order to prevent diffusion ofthe triplet energy in the adjacent phosphorescence emitting layers.Examples of a material used for the space layer include the same asthose used for the hole transporting layer as described above.

Blocking Layer

A blocking layer, such as an electron blocking layer, a hole blockinglayer, or an exciton blocking layer, may be provided adjacent to thelight emitting layer. The electron blocking layer is a layer thatprevents electrons from leaking from the light emitting layer to a holetransporting layer, and the hole blocking layer is a layer that preventsholes from leaking from the light emitting layer to an electrontransporting layer. The exciton blocking layer functions to preventexcitons generated in the light emitting layer from diffusing into thesurrounding layers to trap the excitons within the light emitting layer.

Each layer of the organic EL device can be formed by a conventionallyknown vapor deposition method, a coating method, or the like. Forexample, each layer can be formed by a known technique by a vapordeposition method, such as a vacuum vapor deposition method or amolecular beam vapor deposition method (MBE method), or a coating methodusing a solution of a compound for forming a layer, such as a dippingmethod, a spin-coating method, a casting method, a bar-coating method,and a roll-coating method.

The film thickness of each layer is not particularly limited, but istypically 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm because ingeneral, when the film thickness is too small, defects such as pinholesare likely to occur, and conversely, when the film thickness is toolarge, a high driving voltage is required and the efficiency decreases.

The organic EL device can be suitably used in an electronic instrument,such as a display component of an organic EL panel module or the like, adisplay apparatus of a television, a mobile phone, a personal computer,or the like, and a luminescent apparatus of a lighting or a vehicularlamp.

EXAMPLES

The present invention will be described in more detail below byreference to Examples, but the present invention is not to be limited tothe following Examples.

Inventive Compounds Used for Production of Organic EL Devices ofExamples 1 to 2

Compound 1, Compound 2

Comparative Compound Used for Production of Organic EL Device ofComparative Example 1

Other Compounds Used for Production of Organic EL Devices of Examples 1to 2 and Comparative Example 1

Inventive Compounds Used for Production of Organic EL Devices ofExamples 3 to

Comparative Compounds Used for Production of Organic EL Devices ofComparative Examples 2 to 4

Other Compounds Used for Production of Organic EL Devices of Examples 3to 13 and Comparative Examples 2 to 4

Inventive Compounds Used for Production of Organic EL Devices ofExamples 14 to 19

Comparative Compound Used for Production of Organic EL Device ofComparative Example 5

Other Compounds Used for Production of Organic EL Devices of Examples 14to 19 and Comparative Example 5

Production of Organic EL Device Example 1

A glass substrate of 25 mm×75 mm×1.1 mm with an ITO transparentelectrode (anode) (manufactured by GEOMATEC Co., Ltd.) wasultrasonically cleaned in isopropyl alcohol for 5 minutes and thensubjected to UV ozone cleaning for 30 minutes. The film thickness of theITO was 130 nm.

The cleaned glass substrate with the transparent electrode was mountedon a substrate holder of a vacuum vapor deposition apparatus, andfirstly, Compound HT-1 and Compound HA were vapor co-deposited on thesurface having the transparent electrode formed thereon so as to coverthe transparent electrode, thus forming a hole injecting layer with afilm thickness of 10 nm. The mass ratio of Compound HT-1 and Compound HAwas 97:3.

Subsequently, on the hole injecting layer, Compound HT-1 was vapordeposited to form a first hole transporting layer with a film thicknessof 80 nm.

Subsequently, on this first hole transporting layer, Compound 1 wasvapor deposited to form a second hole transporting layer with a filmthickness of 10 nm.

Subsequently, on this second hole transporting layer, Compound BH-1(host material) and Compound BD-1 (dopant material) were vaporco-deposited to form a light emitting layer with a film thickness of 25nm. The mass ratio of Compound BH-1 and Compound BD-1 (BH-1:BD-1) was96:4.

Subsequently, on this light emitting layer, Compound ET-1 was vapordeposited to form a first electron transporting layer with a filmthickness of 5 nm.

Subsequently, on this first electron transporting layer, Compound ET-2and Liq were vapor co-deposited to form a second electron transportinglayer with a film thickness of 20 nm. The mass ratio of Compound ET-2and Liq (ET-2:Liq) was 50:50.

Subsequently, on this second electron transporting layer, LiF was vapordeposited to form an electron injecting electrode with a film thicknessof 1 nm.

Then, on this electron injecting electrode, metal Al was vapor depositedto form a metal cathode with a film thickness of 50 nm.

The layer configuration of the organic EL device of Example 1 thusobtained was as follows.

ITO (130)/(HT-1:HA=97:3) (10)/HT-1 (80)/Compound 1 (10)/(BH-1:BD-1=96:4)(25)/ET-1 (5)/(ET-2:Liq=50:50) (20)/LiF (1)/Al (50)

In the layer configuration, the numerals in parentheses each indicatethe film thickness (nm), and the ratios are each a mass ratio

Measurement of Device Lifetime (LT95)

The resulting organic EL device was driven with direct current at acurrent density of 50 mA/cm² and the period of time until the luminancewas reduced to 95% of the initial luminance was measured, and wasdefined as 95% lifetime (LT95). The result is shown in Table 1.

Examples 2 and Comparative Example 1

An organic EL device was produced in the same manner as in Example 1except for changing the material of the second hole transporting layerto Compound 2 (Example 2) or Comparative Compound 1 (Comparative Example1), and LT95 was measured. The results are shown in Table 1.

TABLE 1 Material of second hole LT95 (h) at transporting layer 50 mA/cm²Example 1 Compound 1 84 Example 2 Compound 2 77 Comparative Comparative59 Example 1 Compound 1

As apparent from the results in Table 1, the organic EL devicesrespectively containing the inventive compounds (compounds 1 and 2) havea longer lifetime than the organic EL device containing ComparativeCompound 1.

Examples 3

A glass substrate of 25 mm×75 mm×1.1 mm with an ITO transparentelectrode (anode) (manufactured by GEOMATEC Co., Ltd.) wasultrasonically cleaned in isopropyl alcohol for 5 minutes and thensubjected to UV ozone cleaning for 30 minutes. The film thickness of theITO was 130 nm.

The cleaned glass substrate with the transparent electrode was mountedon a substrate holder of a vacuum vapor deposition apparatus, andfirstly, Compound HT-2 and Compound HA were vapor co-deposited on thesurface having the transparent electrode formed thereon so as to coverthe transparent electrode, thus forming a hole injecting layer with afilm thickness of 10 nm. The mass ratio of Compound HT-2 and Compound HA(HT-2:Compound HA) was 97:3.

Subsequently, on the hole injecting layer, Compound HT-2 was vapordeposited to form a first hole transporting layer with a film thicknessof 75 nm.

Subsequently, on this first hole transporting layer, Compound 6 wasvapor deposited to form a second hole transporting layer with a filmthickness of 10 nm.

Subsequently, on this second hole transporting layer, Compound BH-2(host material) and Compound BD-2 (dopant material) were vaporco-deposited to form a light emitting layer with a film thickness of 20nm. The mass ratio of Compound BH-2 and Compound BD-2 (BH-2:BD-2) was99:1.

Subsequently, on this light emitting layer, Compound ET-1 was vapordeposited to form a first electron transporting layer with a filmthickness of 5 nm.

Subsequently, on this first electron transporting layer, Compound ET-3and Liq were vapor co-deposited to form a second electron transportinglayer with a film thickness of 25 nm. The mass ratio of Compound ET-3and Liq (ET-3:Liq) was 50:50.

Subsequently, on this second electron transporting layer, Yb was vapordeposited to form an electron injecting electrode with a film thicknessof 1 nm.

Then, on this electron injecting electrode, metal Al was vapor depositedto form a metal cathode with a film thickness of 80 nm.

The layer configuration of the organic EL device of Example 1 thusobtained was as follows.

ITO (130)/(HT-2:HA=97:3) (10)/HT-2 (75)/Compound 6 (10)/(BH-2:BD-2=99:1)(20)/

ET-1 (5)/(ET-3:Liq=50:50) (25)/Yb (1)/Al (80)

In the layer configuration, the numerals in parentheses each indicatethe film thickness (nm), and the ratios are each a mass ratio.

LT95 of the resulting organic EL device was measured. The result isshown in Table 2.

Examples 4 to 13 and Comparative Examples 2 to 4

An organic EL device was produced in the same manner as in Example 3except for changing the material of the second hole transporting layerto the compound shown in Table 2, and LT95 was measured in the samemanner as in Example 1. The results are shown in Table 2.

TABLE 2 Material of second hole LT95 (h) at transporting layer 50 mA/cm²Example 3 Compound 6  95 Example 4 Compound 7  97 Example 5 Compound 8 108 Example 6 Compound 9  105 Example 7 Compound 10 92 Example 8Compound 11 119 Example 9 Compound 12 110 Example 10 Compound 13 94Example 11 Compound 14 104 Example 12 Compound 15 90 Example 13 Compound19 106 Comparative Comparative 78 Example 2 Compound 2  ComparativeComparative 80 Example 3 Compound 3  Comparative Comparative 63 Example4 Compound 4 

As apparent from the results in Table 2, the organic EL devicescontaining the inventive compounds (compound 6 to 15 and 19) have alonger lifetime than the organic EL devices containing ComparativeCompounds 2 to 4.

Example 14

A glass substrate of 25 mm×75 mm×1.1 mm with an ITO transparentelectrode (anode) (manufactured by GEOMATEC Co., Ltd.) wasultrasonically cleaned in isopropyl alcohol for 5 minutes and thensubjected to UV ozone cleaning for 30 minutes. The film thickness of theITO was 130 nm.

The cleaned glass substrate provided with the transparent electrode wasmounted on a substrate holder of a vacuum vapor deposition apparatus,and firstly, Compound HT-3 and Compound HA were vapor co-deposited onthe surface having the transparent electrode formed thereon so as tocover the transparent electrode, thus forming a hole injecting layerwith a film thickness of 10 nm. The mass ratio of Compound HT-3 andCompound HA (HT-3:HA) was 97:3.

Subsequently, on the hole injecting layer, Compound HT-3 was vapordeposited to form a first hole transporting layer with a film thicknessof 80 nm.

Subsequently, on this first hole transporting layer, Compound 3 wasvapor deposited to form a second hole transporting layer with a filmthickness of 10 nm.

Subsequently, on this second hole transporting layer, Compound BH-1(host material) and Compound BD-1 (dopant material) were vaporco-deposited to form a light emitting layer with a film thickness of 25nm. The mass ratio of Compound BH-1 and Compound BD-1 (BH-1:BD-1) was96:4.

Subsequently, on this light emitting layer, Compound ET-1 was vapordeposited to form a first electron transporting layer with a filmthickness of 5 nm.

Subsequently, on this first electron transporting layer, Compound ET-3and Liq were vapor co-deposited to form a second electron transportinglayer with a film thickness of 20 nm. The mass ratio of Compound ET-3and Liq (ET-3:Liq) was 50:50.

Subsequently, on this second electron transporting layer, LiF was vapordeposited to form an electron injecting electrode with a film thicknessof 1 nm.

Then, on this electron injecting electrode, metal Al was vapor depositedto form a metal cathode with a film thickness of 50 nm.

The layer configuration of the organic EL device of Example 1 thusobtained was as follows.

ITO (130)/(HT-3:HA=97:3) (10)/HT-3 (80)/Compound 3 (10)/(BH-1:BD-1=96:4)(25)/

ET-1 (5)/(ET-3:Liq=50:50) (20)/LiF (1)/Al (50)

In the layer configuration, the numerals in parentheses each indicatethe film thickness (nm), and the ratios are each a mass ratio.

LT95 of the resulting organic EL device was measured. The result isshown in Table 2.

Examples 15 to 19 and Comparative Example 5

An organic EL device was produced in the same manner as in Example 14except for changing the material of the second hole transporting layerto the compound shown in Table 3, and LT95 was measured in the samemanner as in Example 1. The results are shown in Table 3.

TABLE 3 Material of second hole LT95 (h) at transporting layer 50 mA/cm²Example 14 Compound 3  78 Example 15 Compound 4  103 Example 16 Compound5  88 Example 17 Compound 16 81 Example 18 Compound 17 90 Example 19Compound 18 84 Comparative Comparative 65 Example 5 Compound 5 

As apparent from the results in Table 3, the organic EL devicesrespectively containing the inventive compounds (compounds 3 to 5 and 16to 18) have a longer lifetime than the organic EL device containingComparative Compound 5.

Compounds 1 to 19 Synthesized in Synthetic Examples 1 to 19

Intermediate Synthetic Example 1: Synthesis of Intermediate A

(1) Synthesis of Intermediate A-1

In an argon atmosphere, 7.2 g of 2,2,6,6-tetramethylpiperidine and 60 mLof tetrahydrofuran (dehydrated) were put in a flask, and were cooled to−43° C. To the flask, 33 mL of n-BuLi (1.55 M in hexane) was added, andthe mixture was then stirred at −40° C. for 30 minutes. Next, themixture was cooled to −69° C., and 16.0 mL of (iPrO)₃B was added. Afterstirring at −78° C. for 5 minutes, 20 mL of a solution of 5.00 g of1-fluoronaphthalene in THF was added dropwise, and the mixture wasstirred in an ice bath for 10 hours. After completion of the reaction,1N HCl aq. (100 mL) was added, and the mixture was stirred at roomtemperature for 1 hour. Then, the reaction mixture was transferred intoa separating funnel, and was extracted with ethyl acetate. This solutionwas dried over anhydrous magnesium sulfate, then was concentrated andwashed with hexane to obtain 6.13 g (yield 71%) of a white solidof(1-fluoronaphthalen-2-yl)boronic acid (Intermediate A-1).

(2) Synthesis of Intermediate A-2

In an argon atmosphere, 4.52 g of (1-fluoronaphthalen-2-yl)boronic acid(Intermediate A-1), 4.30 g of 2-bromo-1,3-dimethoxybenzene, 0.91 g oftris(dibenzylideneacetone)dipalladium(0), 0.81 g of2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos), 12.6 g oftripotassium phosphate, and 10 mL of toluene (dehydrated) were put in aflask, and were heated under reflux with stirring for 7 hours. Aftercooling to room temperature, the reaction solution was extracted withtoluene, the aqueous layer was removed, and then the organic layer waswashed with saturated saline solution. The organic layer was dried overanhydrous sodium sulfate and was then concentrated. The residue waspurified by silica gel chromatography to obtain 4.70 g (yield 84%) of2-(2,6-dimethoxyphenyl)-1-fluoronaphthalene (Intermediate A-2).

(3) Synthesis of Intermediate A-3

In an argon atmosphere, 4.70 g of2-(2,6-dimethoxyphenyl)-1-fluoronaphthalene (Intermediate A-2) and 210mL of dichloromethane (dehydrated) were put in a flask and were cooledto 0° C. Tb the flask, 41 mL of a 1.0 mol/l boron tribromidedichloromethane solution was added, and then the mixture was stirred atroom temperature for 4 hours. After completion of the reaction, thesolution was cooled to −78° C., was carefully deactivated with methanol,and was further deactivated with a sufficient amount of water. Thesolution was transferred into a separating funnel, was extracted withdichloromethane, and was dried over anhydrous sodium sulfate. Then, thesolution was allowed to pass through a silica gel short column to removeorigin impurities, and the solution was concentrated. The resultingsample was dried in vacuum at room temperature for 3 hours to obtain4.00 g (94%) of a transparent oily substance of2-(3-fluoronaphthalen-2-yl)benzene-1,3-diol (Intermediate A-3).

(4) Synthesis of Intermediate A-4

In an argon atmosphere, 4.00 g of2-(3-fluoronaphthalen-2-yl)benzene-1,3-diol (Intermediate A-3), 15 mL ofN-methyl-2-pyrrolidinone (dehydrated), and 3.26 g of K₂CO₃ were put in aflask, and were then stirred at 150° C. for 2 hours. After completion ofthe reaction, the solution was cooled to room temperature, ethyl acetate(200 mL) was added, and the mixture was transferred into a separatingfunnel and was washed with water. The solution was dried over anhydroussodium sulfate and was then purified by silica gel chromatography toobtain 1.25 g (yield 34%) of a white solid ofnaphtho[1,2-b]benzofuran-7-ol (Intermediate A-4).

(5) Synthesis of Intermediate 5

In an argon atmosphere, 1.25 g naphtho[1,2-b]benzofuran-7-ol(Intermediate A-4), 65 mg of N,N-dimethyl-4-aminopyridine, 1.08 mL oftrifluoromethane sulfonic anhydride, and 27 mL of dichloromethane(dehydrated) were put in a flask and were cooled to 0° C. 10.6 mL ofpyridine (dehydrated) was added dropwise, and then the mixture wasstirred at room temperature for 2 hours. After completion of thereaction, the reaction mixture was deactivated with a sufficient amountof water. The solution was transferred into a separating funnel, wasextracted with dichloromethane, and was dried over anhydrous sodiumsulfate. Then, the solution was allowed to pass through a silica gelshort column to remove origin impurities and the solution wasconcentrated. The resulting sample was dried in vacuum at roomtemperature for 3 hours to obtain 1.50 g (77%) of a white solid ofnaphtho[1,2-b]benzofuran-7-yl trifluoromethane sulfonate (IntermediateA).

Intermediate Synthetic Example 2: Synthesis of Intermediate B

In an argon atmosphere, a mixture of 7.33 g (20.0 mmol) of IntermediateA, 3.75 g (24.0 mmol) of 4-chlorophenylboronic acid, 0.327 g (0.400mmol) of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloridedichloromethane additive, 20 mL (40.0 mmol) of 2M aqueous sodiumcarbonate solution, and 66.7 mL of DME was stirred at 80° C. for 2hours. The reaction solution was cooled to room temperature. Water wasadded thereto, followed by filtration. The resulting residue waspurified by silica gel chromatography and recrystallization to obtain6.07 g of a white solid. The yield was 92%.

Intermediate Synthetic Example 3: Synthesis of Intermediate C

A white solid was obtained in the same manner as in IntermediateSynthetic Example 2 except for using 3-chlorophenylboronic acid insteadof 4-chlorophenylboronic acid. The yield was 94%.

Intermediate Synthetic Example 4: Synthesis of Intermediate D

A white solid was obtained in the same manner as in IntermediateSynthetic Example 2 except for using 2-chlorophenylboronic acid insteadof 4-chlorophenylboronic acid. The yield was 90%.

Intermediate Synthetic Example Synthesis of Intermediate E

A white solid was obtained in the same manner as in IntermediateSynthetic Example 2 except for using(4′-chloro[1,1′-biphenyl]-2-yl)boronic acid instead of4-chlorophenylboronic acid. The yield was 77%.

Intermediate Synthetic Example 6: Synthesis of Intermediate F

In an argon atmosphere, a mixture of 9.73 g (30.0 mmol) ofN-(4-bromophenyl)[1,1′-biphenyl]-4-amine, 8.19 g (33.0 mmol) of(3-(naphthalen-1-yl)phenyl)boronic acid, 0.425 g (0.60 mmol) ofbis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium(II),30 mL (60.0 mmol) of 2M aqueous sodium carbonate solution, and 150 mL ofDME was stirred with heat at 80° C. for 4 hours. The reaction solutionwas cooled to room temperature, and then was concentrated under reducedpressure. The resulting residue was purified by silica gelchromatography to obtain 8.06 g of a white solid. The yield was 60%.

Intermediate Synthetic Example 7: Synthesis of Intermediate G

In an argon atmosphere, a mixture of 5.68 g (25.9 mmol) of3-(1-naphthalenyl)benzene amine, 6.58 g (25.9 mmol) of1-iodonaphthalene, 0.474 g (0.518 mmol) oftris(dibenzylideneacetone)dipalladium(0), 0.645 g (1.04 mmol) of BINAP,2.74 g (28.5 mmol) of sodium-t-butoxide, and 130 mL of toluene wasstirred at 100° C. for 7 hours. The reaction solution was cooled to roomtemperature, and was then concentrated under reduced pressure. Theresulting residue was purified by silica gel chromatography to obtain8.95 g of a white solid. The yield was 84%.

Intermediate Synthetic Example 8: Synthesis of Intermediate H

A white solid was obtained in the same manner as in the Synthesis ofIntermediate G except for using 1-(4-bromophenyl)naphthalene instead of1-iodonaphthalene. The yield was 79%.

Synthetic Example 1: Synthesis of Compound 1

In an argon atmosphere, a mixture of 2.25 g (7.00 mmol) ofN-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine, 2.53 g (7.70 mmol) ofIntermediate B, 0.128 g (0.140 mmol) oftris(dibenzylideneacetone)dipalladium(0), 0.162 g (0.56 mmol) oftri-t-butylphosphonium tetrafluoroborate, 0.942 g (9.80 mmol) ofsodium-t-butoxide, and 70 mL of xylene was stirred at 110° C. for 2hours. The reaction solution was cooled to room temperature, and wasthen concentrated under reduced pressure. The resulting residue waspurified by silica gel chromatography and recrystallization to obtain3.51 g of a white solid. The yield was 82%.

The resulting substance was revealed as Compound 1 by mass spectrometry,showing m/e=614 with respect to the molecular weight of 613.76.

Synthetic Example 2: Synthesis of Compound 2

A white solid was obtained in the same manner as in Synthetic Example 1except for using Intermediate C instead of Intermediate B. The yield was92%.

The resulting substance was revealed as Compound 2 by mass spectrometry,showing m/e=614 with respect to the molecular weight of 613.76.

Synthetic Example 3: Synthesis of Compound 3

In an argon atmosphere, a mixture of 0.986 g (4.02 mmol) of [1,1′:4′,1″-terphenyl]-4-amine, 2.91 g (8.85 mmol) of Intermediate B, 0.110 g(0.121 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.140 g (0.482mmol) of tri-t-butylphosphonium tetrafluoroborate, 1.08 g (11.3 mmol) ofsodium-t-butoxide, and 80 mL of toluene was stirred under reflux at theboiling point for 2 hours. The reaction solution was cooled to roomtemperature, and was then concentrated under reduced pressure. Theresulting residue was purified by recrystallization to obtain 2.35 g ofa white solid. The yield was 70%.

The resulting substance was revealed as Compound 3 by mass spectrometry,showing m/e=830 with respect to the molecular weight of 830.00.

Synthetic Example 4: Synthesis of Compound 4

A white solid was obtained in the same manner as in Synthetic Example 1except for usingN-([1,1′-biphenyl]-4-yl-2,3,5,6-d4)-[1,1′-biphenyl-2,3,5,6-d4]-4-amineinstead of N-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine. The yield was81%.

The resulting substance was revealed as Compound 4 by mass spectrometry,showing m/e=622 with respect to the molecular weight of 621.81.

Synthetic Example 5: Synthesis of Compound 5

A white solid was obtained in the same manner as in Synthetic Example 1except for using 4-(1-naphthalenyl)-N-[4-(1-naphthalenyl)phenyl]benzeneamine instead of N-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine andchanging the reaction temperature to 130° C. The yield was 61%.

The resulting substance was revealed as Compound 5 by mass spectrometry,showing m/e=714 with respect to the molecular weight of 713.88.

Synthetic Example 6: Synthesis of Compound 6

A white solid was obtained in the same manner as in Synthetic Example 1except for using 4-(2-naphthalenyl)-N-[4-(2-naphthalenyl)phenyl]benzeneamine instead of N-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine andchanging the reaction temperature to 120° C. The yield was 61%.

The resulting substance was revealed as Compound 6 by mass spectrometry,showing m/e=714 with respect to the molecular weight of 713.88.

Synthetic Example 7: Synthesis of Compound 7

A white solid was obtained in the same manner as in Synthetic Example 1except for using N-[1,1′-biphenyl]-4-yl-[1,1′:4′,1″-terphenyl]-4-amineinstead of N-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine and changingthe reaction temperature to 130° C. The yield was 63%.

The resulting substance was revealed as Compound 7 by mass spectrometry,showing m/e=690 with respect to the molecular weight of 689.86.

Synthetic Example 8: Synthesis of Compound 8

A white solid was obtained in the same manner as in Synthetic Example 1except for using Intermediate D instead of Intermediate B and usingSPhos instead of tri-t-butylphosphonium tetrafluoroborate. The yield was83%.

The resulting substance was revealed as Compound 8 by mass spectrometry,showing m/e=614 with respect to the molecular weight of 613.76.

Synthetic Example 9: Synthesis of Compound 9

A white solid was obtained in the same manner as in Synthetic Example 8except for using N-[4-(1-naphthalenyl)phenyl][1,1′-biphenyl]-4-amineinstead of N-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine. The yield was89%.

The resulting substance was revealed as Compound 9 by mass spectrometry,showing m/e=664 with respect to the molecular weight of 663.82.

Synthetic Example 10: Synthesis of Compound 10

A white solid was obtained in the same manner as in Synthetic Example 8except for using 4-(1-naphthalenyl)-N-[4-(1-naphthalenyl)phenyl]benzeneamine instead of N-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine. Theyield was 64%.

The resulting substance was revealed as Compound 10 by massspectrometry, showing m/e=714 with respect to the molecular weight of713.88.

Synthetic Example 11: Synthesis of Compound 11

A white solid was obtained in the same manner as in Synthetic Example 8except for usingN-([1,1′-biphenyl]-4-yl-2,3,5,6-d4)-[1,1′-biphenyl-2,3,5,6-d4]-4-amineinstead of N-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine. The yield was71%.

The resulting substance was revealed as Compound 11 by massspectrometry, showing m/e=622 with respect to the molecular weight of621.81.

Synthetic Example 12: Synthesis of Compound 12

A white solid was obtained in the same manner as in Synthetic Example 8except for using Intermediate E instead of Intermediate D. The yield was91%.

The resulting substance was revealed as Compound 12 by massspectrometry, showing m/e=690 with respect to the molecular weight of689.86.

Synthetic Example 13: Synthesis of Compound 13

A white solid was obtained in the same manner as in Synthetic Example 8except for using N,9,9-triphenyl-9H-fluoren-2-amine instead ofN-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine. The yield was 47%.

The resulting substance was revealed as Compound 13 by massspectrometry, showing m/e=702 with respect to the molecular weight of701.87.

Synthetic Example 14: Synthesis of Compound 14

A white solid was obtained in the same manner as in Synthetic Example 8except for using Intermediate F instead ofN-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine. The yield was 75%.

The resulting substance was revealed as Compound 14 by massspectrometry, showing m/e=740 with respect to the molecular weight of739.92.

Synthetic Example 15: Synthesis of Compound 15

A white solid was obtained in the same manner as in Synthetic Example 1except for using Intermediate G instead ofN-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine. The yield was 68%.

The resulting substance was revealed as Compound 15 by massspectrometry, showing m/e=638 with respect to the molecular weight of637.78.

Synthetic Example 16: Synthesis of Compound 16

A white solid was obtained in the same manner as in Synthetic Example 1except for using Intermediate H instead ofN-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine. The yield was 62%.

The resulting substance was revealed as Compound 16 by massspectrometry, showing m/e=714 with respect to the molecular weight of713.88.

Synthetic Example 17: Synthesis of Compound 17

A white solid was obtained in the same manner as in Synthetic Example 8except for usingN-[3-(1-naphthalenyl)phenyl][1,1′:4′,1″-terphenyl]-4-amine instead ofN-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine. The yield was 75%.

The resulting substance was revealed as Compound 17 by massspectrometry, showing m/e=740 with respect to the molecular weight of739.92.

Synthetic Example 18: Synthesis of Compound 18

A white solid was obtained in the same manner as in Synthetic Example 1except for using 4-(4-dibenzofranyl)-N-[4-(1-naphthalenyl)phenyl]benzeneamine instead of N-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine. Theyield was 66%.

The resulting substance was revealed as Compound 16 by massspectrometry, showing m/e=754 with respect to the molecular weight of753.90.

Synthetic Example 19: Synthesis of Compound 19

A white solid was obtained in the same manner as in Synthetic Example 8except for using N-[1,1′-biphenyl]-4-yl-9,9-dimethyl-9H-fluoren-2-amineinstead of N-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine. The yield was61%.

The resulting substance was Compound 19 by mass spectrometry, showingm/e=654 with respect to the molecular weight of 653.83.

REFERENCE SIGNS LIST

-   -   1, 11: Organic EL device    -   2: Substrate    -   3: Anode    -   4: Cathode    -   5: Light emitting layer    -   6: Hole transporting zone (hole transporting layer)    -   6 a: Hole injecting layer    -   6 b: First hole transporting layer    -   6 c: Second hole transporting layer    -   7: Electron transporting zone (Electron transporting layer)    -   7 a: First electron transporting layer    -   7 b: Second electron transporting layer    -   10, 20: Light emitting unit

The invention claimed is:
 1. A compound represented by the followingformula (1):

wherein R¹ to R⁹ are each independently a hydrogen atom, a substitutedor unsubstituted alkyl group baying 1 to 50 carbon atoms, a substitutedor unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, ahalogen atom, a cyano group, a nitro group, or a substituted orunsubstituted heterocyclic group having 5 to 50 ring atoms, providedthat adjacent two selected from R¹ to R⁹ are not bonded to each other,thus forming no ring structure, L¹ is an arylene group represented bythe following formula:

wherein each * represents a bonding site to the carbon atom or thecentral nitrogen atom, and Q₁ to Q₄ are each independently a hydrogenatom, L² and L³ are each independently a single bond, a substituted orunsubstituted divalent heterocyclic group having 5 to 30 ring atoms, ora group represented by any of the following formulae (i) to (iii):

wherein *a is bonded to one selected from the carbon atoms *1 to *3, *bis bonded to one selected from the carbon atoms *4 to *6, *c is bondedto one selected from the carbon atoms *7 to *9, *d is bonded to oneselected from the carbon atoms *10 to *17, *e is bonded to another oneselected from the carbon atoms *10 to *17, * represents a bonding siteto the central nitrogen atom, and ** represents a bonding site to Ar¹ orAr², Ar¹ and Ar² are each independently a group represented by any ofthe following formulae (a) to (e):

in the formula (a), R¹⁰ to R²⁵ are each independently a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 50 carbon atoms, asubstituted or unsubstituted cycloalkyl group having 3 to 50 ring carbonatoms, a halogen atom, a cyano group, a nitro group, a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms constitutedonly of 6-membered rings, or a substituted or unsubstituted heterocyclicgroup having 5 to 50 ring atoms, provided that one selected from R¹⁰ toR¹⁴ is a single bond bonded to *f, one selected from R¹⁵ to R²⁰ is asingle bond bonded to *g, another one selected from R¹⁵ to R²⁰ is asingle bond bonded to *h, *** represents a bonding site to L² or L³, m1is 0 or 1, n1 is 0 or 1, when m1 is 0 and n1 is 0, *h is bonded to L² orL³, when m1 is 0 and n1 is 1, *f is bonded to L² or L³, when m1 is 1 andn1 is 0, one selected from R¹⁰ to R¹⁴ is a single bond bonded to *h, k1is 1 or 2, and adjacent two selected from R¹⁰ to R¹⁴ that are not thesingle bond are, and adjacent two selected from R¹⁵ to R²⁰ that are noteither of the single bonds are, not bonded to each other, thus formingno ring structure; in the formula (b), R¹⁰ to R²⁰, *f, *g, *h, and ***are the same as described above, R²⁶ to R³³ are each independently ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50carbon atoms, a substituted or unsubstituted cycloalkyl group having 3to 50 ring carbon atoms, a halogen atom, a cyano group, a nitro group, asubstituted or unsubstituted aryl group having 6 to 30 ring carbon atomsconstituted only of 6-membered rings, or a substituted or unsubstitutedheterocyclic group having 5 to 50 ring atoms, provided that one selectedfrom R²⁶ to R³³ is a single bond bonded to *i, m2 is 0 or 1, n2 is 0 or1, when m2 is 0 and n2, is 0, *h is bonded to L² or L³, when m2 is 0 andn2 is 1; *f is bonded to L² or L³, when m2 is 1 and n2 is 0, oneselected from R¹⁰ to R¹⁴ is a single bond bonded to *h, and adjacent twoselected from R¹⁰ to R¹⁴ that are not the single bond are, and adjacenttwo selected from R¹⁵ to R²⁰ that are not either of the single bondsare, not bonded to each other, thus forming no ling structure; in theformula (c), R¹⁰ to R²⁰, *f, *g, *h, and *** are the same as describedabove, R³⁴ to R⁴³ are each independently a hydrogen atom, a substitutedor unsubstituted alkyl group having 1 to 50 carbon atoms, a substitutedor unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, ahalogen atom, a cyano group, a nitro group, a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms constitutedonly of 6-membered rings, or a substituted or unsubstituted heterocyclicgroup having 5 to 50 ring atoms, provided that one selected from R³⁴ tois a single bond bonded to *j, m3 is 0 or 1, n3 is 0 or 1, when m3 is 0and n3 is 0, *h is bonded to or L³, when m3 is 0 and n3 is 1, *f isbonded to L² or L³, when m3 is 1 and n2 is 0, one selected from R¹⁰ toR¹⁴ is a single bond bonded *h, and adjacent two selected from R¹⁰ toR¹⁴ that are not the single bond are, adjacent two selected from R¹⁵ toR²⁰ that are not either of the single bonds are, and R³⁴ and R³⁵ are,not bonded to each other, thus forming no ring structure; in the formula(d), R¹⁰ to R¹⁴, *f, and *** are the same as described above, R⁴⁴ to R⁵¹are each independently a hydrogen atom, a substituted or unsubstitutedalkyl group having 1 to 50 carbon atoms, a substituted or unsubstitutedcycloalkyl group having 3 to 50 ring carbon atoms, a halogen atom, acyano group, a nitro group, a substituted or unsubstituted aryl grouphaving 6 to 30 ring carbon atoms constituted only of 6-membered rings,or a substituted or unsubstituted heterocyclic group having 5 to 50 ringatoms, X is an oxygen atom, a sulfur atom, CR^(a)R^(b), or NW, R^(a),R^(b), and R^(c) are each independently a hydrogen atom, a substitutedor unsubstituted alkyl group having 1 to 50 carbon atoms, a substitutedor unsubstituted aryl group having 6 to 50 ring carbon atoms, or asubstituted or unsubstituted heterocyclic group having 5 to 50 ringatoms, provided that one selected from R⁴⁴ to R⁵⁴ and R^(c) is a singlebond bonded to *k, m4 is 0 or 1, when m4 is 0, *f is bonded to L² or L³,combinations of adjacent two selected from R⁴⁴ to R⁵¹ that are not thesingle bond may each independently be bonded to each other to form asubstituted or unsubstituted ring structure, R⁴⁶ and R⁴⁷, and R⁴⁸ andR⁴⁹, are not bonded to each other, thus forming no ring structure, andR^(a) and R^(b) are not crosslinked; in the formula (e), R¹⁰ to R¹⁴, *f,and *** are the same as described above, R⁵² to R⁶⁶ are eachindependently a hydrogen atom, a substituted or unsubstituted alkylgroup having 1 to 50 carbon atoms, a substituted or unsubstitutedcycloalkyl group having 3 to 50 ring carbon atoms, a halogen atom, acyano group, a nitro group, a substituted or unsubstituted aryl grouphaving 6 to 30 ring carbon atoms constituted only of 6-membered rings,or a substituted or unsubstituted heterocyclic group having 5 to 50 ringatoms, provided that one selected from R⁵² to R⁵⁶ is a single bondbonded to *1, another one selected from R⁵² to R⁵⁶ is a single bondbonded to *m, m5 is 0 or 1, when m5 is 0, *f is bonded to L² or L³,adjacent two selected from R¹⁰ to R¹⁴ that are not the single bond are,adjacent two selected from R⁵² to R⁵⁶ that are not either of the singlebonds are, R⁵² and R⁶¹ are, and R⁵⁶ and R⁵⁷ are, not bonded to eachother, thus forming no ring structure.
 2. The compound according toclaim 1, wherein Ar¹ and Ar² are each independently a group representedby any of the formulae (a-1) to (e-1):

wherein R¹⁰, R¹¹, R¹³, R¹⁴, R¹⁵, to R¹⁹, R²¹ to R⁶⁶, X, *i, *j, *k, *l,*m, m1, n1, k1, m2, n2, m3, n3, m4, and m5 are as defined in the formula(1).
 3. The compound according to claim 1, wherein at least one of Ar¹and Ar² is a group represented by the formula (a).
 4. The compoundaccording to claim 1, wherein L² and L³ are each independently a singlebond, a group represented by the formula (i) or (ii).
 5. The compoundaccording to claim 1, wherein *a is bonded to the carbon atom *3.
 6. Thecompound according to claim 1, wherein *b is bonded to the carbon atom*6.
 7. The compound according to claim 1, wherein *c is bonded to thecarbon atom *7.
 8. The compound according to claim 1, wherein X is anoxygen atom, CR^(a)R^(b), or C.
 9. The compound according to claim 1,wherein R or R³⁷ is a single bond bonded to *j.
 10. The compoundaccording to claim 1, wherein R⁵³ is a single bond bonded to *l and R⁵⁶is a single bond bonded to *m.
 11. The compound according to claim 1,wherein all of R¹ to R⁹ are each a hydrogen atom.
 12. The compoundaccording to claim 1, wherein in the formula (a), all of R¹⁰ to R¹⁴ thatare not the single bond bonded to *f are each a hydrogen atom.
 13. Thecompound according to claim 1, wherein in the formula (a), all of R¹⁵ toR²⁰ that are not the single bond bonded to *g nor the single bond bondedto *h are each a hydrogen atom.
 14. The compound according to claim 1,wherein all of R²¹ to R²⁵ are each a hydrogen atom.
 15. The compoundaccording to claim 1, wherein in the formula (b), all of R¹⁰ to R¹⁴ thatare not the single bond bonded to *f are each a hydrogen atom.
 16. Thecompound according to claim 1, wherein in the formula (b), all of R¹⁵ toR²⁰ that are not the single bond bonded to *g nor the single bond bondedto *h are each a hydrogen atom.
 17. The compound according to claim 1,wherein all of R²⁶ to R³³ that are not the single bond bonded to *i areeach a hydrogen atom.
 18. The compound according to claim 1, wherein thecompound represented by the formula (1) comprises at least one deuteriumatom.
 19. A material for organic electroluminescence devices, thematerial comprising the compound according to claim
 1. 20. An organicelectroluminescence device comprising a cathode, an anode, and anorganic layer between the cathode and the anode, the organic layercomprising a light emitting layer, and at least one layer of the organiclayer comprises the compound according to claim
 1. 21. The organicelectroluminescence device according to claim 20, wherein the organiclayer comprises a hole transporting zone between the anode and the lightemitting layer, the hole transporting zone comprises the compound. 22.The organic electroluminescence device according to claim 21, whereinthe hole transporting zone comprises a first hole transporting layer onan anode side and a second hole transporting layer on a cathode side,the first hole transporting layer, the second hole transporting layer,or both comprise the compound.
 23. The organic electroluminescencedevice according to claim 22, wherein the second hole transporting layercomprises the compound.
 24. The organic electroluminescence deviceaccording to claim 22, wherein the second hole transporting layer isadjacent to the light emitting layer.
 25. The organicelectroluminescence device according to claim 20, wherein the lightemitting layer comprises a fluorescent dopant material.
 26. The organicelectroluminescence device according to claim 20, wherein the lightemitting layer comprises a phosphorescent dopant material.
 27. Anelectronic instrument comprising the organic electroluminescence deviceaccording to claim
 20. 28. The compound according to claim 1, wherein inthe formula (d), adjacent two selected from R⁴⁴ to R⁵¹ that are not thesingle bond are not bonded to each other, thus forming no ringstructure.